


Breaking Point

by Girl_WithTheDirtyMind



Series: Dirty, Sexy Times: You/Dean Winchester [5]
Category: Supernatural
Genre: Anger, Angst, Begging, Bondage, Claiming/Marking, Cocky Dean, Conflicted Reader, Confusion, Crowley Being an Asshole, Crying, Daddy Kink, Dean Talks Dirty, Demon Dean Being an Asshole, Demon Powers, Denial of Feelings, Dildos, Dom/sub Play, Emotional Hurt, Explicit Language, Explicit Sexual Content, F/M, Fear, Fear Play, Forced Orgasm, Frightened Reader, Goodbye Sex, Grief/Mourning, Hair-pulling, Hell, Hopeful Ending, Hurt No Comfort (at first), Intimidation, Kidnapping, Kink Discovery, Loss of Control, Manipulation, Mental Instability, Minor Humiliation, Minor pain play, Minor phobia, Multiple Orgasms, Orgasm Denial, Original Demonic Powers, Overstimulation, Painful Sex, Plot What Plot/Porn Without Plot, Porn With Plot, Provoked Violence, Punishment, Pussy Spanking, Rape/Non-con Elements, Riding Crops, Roughness, Rules, Sad (sort of), Sam Humor, Scary Dean Winchester, Sexual Coercion, Sexy Dean, Singing, Smut, Some Humor, Song Lyrics, Spanking, Tears, Threats, Torturer Dean, Under-negotiated Kink(s), Vaginal Fingering, Vibrators, Winchester Feels, minor torture, sam is a giant, twisted feelings
Language: English
Status: Completed
Published: 2015-09-26
Updated: 2015-12-20
Packaged: 2018-04-22 20:26:08
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 41,036
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4849343
Author URL: https://archiveofourown.org/users/Girl_WithTheDirtyMind/pseuds/Girl_WithTheDirtyMind
Summary: <blockquote class="userstuff">
              <p>Demon Dean needs a victim to satiate the Mark of Cain, and you are the lucky candidate. Will you become another bloody casualty of his deep rooted anger, or will he find a more pleasurable use for you? </p><p>Tagged chapter by chapter. Enjoy~ </p><p>Demon!Dean Fic.</p>
            </blockquote>





	1. I'm In Hell.

**Author's Note:**

> It's finally here! The one I've been promising! 
> 
> **Triggers** Dean is extremely frightening to reader, especially at first. There will be a lot of emotional battles and mental manipulation in this fic. If Non-Con is a trigger for you, as with all of my fics, please proceed with caution. I don't want to scar ya ;) And the first two chapters with be set in Hell, even though Reader is human. If that is upsetting to you, be careful out there.
> 
> Okay, with all of that out of the way, enjoy enjoy enjoy my little smut addicts!

You were sitting at the bar nursing a half empty beer, talking with a man who had a wonderfully sophisticated English accent and a fancy tailored black suit coupled with a muted purple tie.

He was smart, witty, and refreshing to talk to since it was very likely that he was the least limy looking fellow in the bar. So at the moment you weren’t worried about the fact that he wasn’t exactly your type, it just seemed harmless to make conversation.

Besides he didn’t really seem interested in you that way either, you got the feeling he was just content with minor flirting and mutual compliments which was making your night a lot less difficult.

Having just lost your dream job you were foolishly trying to drink your depression away as if you weren’t aware alcohol in _itself_ was a depressant. The man named Crowley was a nice distraction, you felt no pressure with the kind charming British man, therefore no warning sirens were going off. If you only knew.

If you only knew that Crowley had perfected his mind diluting charisma over centuries of manipulation. . . You were falling right into his perfectly crafted web, and hadn’t a hint it was happening to you. With a halfhearted sigh you decided to go back to your cozy apartment and snuggle up with some popcorn in front of your laptop, to remind yourself why Meg Ryan wasn’t getting any sleep in Seattle.

_Yeah, that sounds pathetically blissful right about now._

As soon as you stood up Crowley pushed back his barstool quickly to do the same. In the back of your mind you remembered that it was considered courteous to stand when a lady did, and you were once again surprised at the man’s barefaced respect he continued showing you.

“Oh um you didn’t have to do that. . .” you giggled a little feeling a buzz through the headrush that came from standing. He regarded you with a sideways doting look,

“Now darling, what kind of Gentleman would I be if I abandoned my virtue?” it was spoken like it was the most obvious thing in the world, and he had you smiling again.

“You _are_ that Crowley,” you informed him and when he raised a brow you clarified, “a Gentleman that is.”

“Exactly my point. Now.” he moved to take your jacket from the hook on the bar like it was second nature, “Don’t forget your coat dear, there’s a bit of a bite out.”

You could listen to the way he spoke all night, that colorful voice of his just sounded so intelligent. You turned around so he could slip your jacket on for you, and couldn’t help but smile.

_He is so damned polite!_

There was no way you could foresee the dark turn your night was about to take,

“I would never forgive myself if I didn’t offer to walk you to your car,” he started with his dark brown eyes promising genuine safety, “a pretty duck like you might run into a spot of trouble along the way this late at night.” Normally you would have declined, but he was right. This neighborhood was notoriously shotty and your car was parked a good three blocks away,

“Um. . . Yeah sure why not?” you smiled kindly, “Better safe than sorry right?” instead of a verbal answer Crowley gave you a little wink and took your arm to gently lead you through the door, yet another chivalrous gesture that had you grinning like an idiot and feeling like a queen.

The walk to your car was filled with easy conversation and unabashed charm from the obviously experienced man.

He had you looking up at him in wonder under the dim streetlights, he was only about two inches taller than you, but he seemed so sure of himself that you didn’t even think about the shady alleyways you strolled by in his presence. The same shady alleyways that tempted you to walk in the center of the street when you were on your own.

Out of nowhere the British man stopped and connected his brown eyes with your (e/c) ones, and for the first time they held a glint of something sinister. Like he had disturbing secret. It made your throat catch in surprise,

“I’ve had a wonderful evening with you love, and while I did enjoy our chats immensely, it pains me to tell you I have to ruin it.” your mouth hung open dumbly, and he looked over the top of your head to squint at nothing, as if something in his head was causing him pain.

“Don’t panic blueberry,” it was a gentle whisper, “this will only cause minor discomfort.” you were still too stunned to move or speak.

_How did he play me so well?_

He pulled you close so abruptly it made you grunt, and touched two fingers to your head, immediately overtaking your mind with painful pressure and your vision with blurred tumbling scenery.

Your feet felt swept from under you, but you weren’t necessarily falling. The whole shebang ended as soon as it started and you found yourself stumbling like a drunkard as soon as your feet hit a hard-packed dirt floor.

Threats of vomiting rolled your stomach uncomfortably and you clutched your midsection with a grimace.

_What the Hell is happening?_

**_~_ **

“Easy puppet.” Crowley’s silky voice invaded your ringing ears, and you forced yourself to look up, “Take some deep breaths, the feeling will be gone momentarily.” you ignored his advice,

“What the Hell did you do?” you practically screamed at him, “What is this?” you coughed on the burn of stomach acid and pulled oxygen in deeply, trying to stand upright. It smelled like a mixture of mildew and death in this new place.

A spine tingling chuckle sounded somewhere near you and the register was too deep to have been Crowley. Whirling around you locked wide eyes with a man on the far side of the room.

 _No. . . not room. . . a cell._ It looked like a prison cell, but with like ten times more space and moist rotting walls.  _Oh fuck what is this?_ The chuckling man was cloaked in shadows and you strained to see what he looked like. He spoke,

“Goddamn, I knew she was a good choice,” he was speaking to Crowley now, “she’s a sexy little thing ain’t she.” your gaze shot back up to the British man, terror gripping your soul. Crowley only glanced at you passively,

“Glad to know she’ll fulfill your needs,” he was a far cry from who you’d been chatting with all night, like he was a new man. An evil one.

“Are we done here squirrel? I have some other business around The Basement to attend.” he said it like he couldn’t care less about any of this,

“Cr - _Crowley_?” you stuttered quietly, and he finally turned his gaze down to your frightened expression. He looked slightly guilty and he spoke softly to you,

“So sorry dear, I’m afraid I haven’t properly introduced myself.” you waited without breathing, “Crowley, King of Hell.” he swaggered a little at the title and you paled,

“No. . No you’re _lying_.” you murmured knowing in your heart it was true, “What is this?” he never looked away from you,

“You’re here to satiate the Mark of Cain my sweet,” he spoke like he was reading poetry, “to feed Dean’s bloodlust so he can be of use to me. I’m afraid your life is over.” You felt like your heart stopped, like the world froze, like every molecule of Oxygen shunned your lungs.

Crowley rolled his eyes up to the ceiling as if he might find the right words up there,

“I guess you can think of him as your own personal torturer. . Yes that sounds about right.” his gaze traveled back down to pin you with an apologetic smirk that made you want to scream. 

Finally you snapped to your senses and backed away from the King of Hell, whipping your head back and forth in denial while trying to comprehend his words. However as soon as your back hit someone warm and solid your mind was wiped clean by the force of your terror. As you turned to face your new tormentor, you hedged away to avoid pain or really any kind of touching for that matter.

“Heya sweetheart.” he was menacingly tall. And muscular. And at first glance _wildly_ sexy, but you stomped out that thought as soon as it came, because the powerful looking man was smirking down at you with green eyes that promised two things: Pain and ill intent.

It absolutely took your breath away. You stumbled backward away from him on the dirt floor, and he gave you the few feet you needed to give you a false sense of security.

“Stay the Hell away from me,” Jesus you sounded pathetic already, and the dark chuckle he gave was enough to draw frightened tears to your eyes, but you wouldn’t allow yourself to beg. 

Not yet anyway.

The man was wearing dark leather boots, probably steel-toed, that were partially covered by a pair of well-worn dark wash jeans. A black cotton t-shirt that emphasized his already muscular body and his powerful biceps were covered with a red button down shirt that he had left open with the sleeves rolled.

You continued scanning his body until you were able to look up and really take in your kidnapper. A strong jawline with stubble along the edge framed a pair of very sexy looking lips.  _Lock it up idiot. Now’s not the time._ But it was hard not to notice what with how long it had been since you'd been with someone. All your energy was focused on your job up until today, and you had forgotten how to really live because of it.

So yeah. You noticed this guy was the walking definition of sex. Big deal.

In fact there was no _denying_ that he was attractive, and big too. _Really_ fucking tall, his lean frame dwarfed you which was actually all manner of intimidating. You lifted your gaze past the freckles on his cheeks and nose up to his now. . . black filled eyes. . . You gave a stuttering gasp,

“What _are_ you?” you squeaked and wrapped your arms around your trembling body. He smiled widely, flashing his gleaming white teeth,

“Oh baby,” his voice was husky, rough, and deep. “I’m a demon.” your eyes glossed over with more stubborn tears, and you shook your head miserably trying to fight them off,

“This _can’t_ be real. No. . . this can’t be _happening_!” you cried into the echoing stone cell. Again he chuckled in a way that made your spine tingle, and allowed the black in his eyes to recede which gave you a minuscule amount of comfort. “Crowley!” you turned sideways slightly to beg the British man to let you go, but were met with only empty air. He was gone.

And you were alone with a sadist.

“Name’s Dean Winchester,” he spoke easily and nodded cockily when you timidly looked back to him, “you and I are gonna have some fun together sweetcheeks.” You were too busy trying fruitlessly to calm yourself down to offer your name, but he most likely didn’t care for it anyway.

Dean’s electric green eyes seemed to catalog the way your body was shaking, and the way your eyes were darting around nervously, and to your ever-growing horror he looked _pleased_.

“Oh come on, don’t look so scared sweetheart,” he grumbled like this was an everyday thing, then smiled softly. It wasn’t comforting, “I just wanna play with my new toy. Promise I’ll be gentle. . .” Your eyes pooled at the implication in his words, and terror from gripped your gut. His expression darkened and his eyes flooded black again. You whimpered at the sight, unsure what made him angry, and backed away - looking quickly to the floor.

“Aren’t you gonna say thank you slut?” he growled angrily, 

“Th - thank you.” you quickly stuttered, earning you a smile. You weren't even sure what you were thanking him for, you just wanted him to stop glaring. 

“Th - thank you _what_?” he mocked with a sick grin. You were at a loss and you swallowed multiple times before he took pity on your confusion, “Sir baby. Call me Sir." You blinked back insistent tears, having a sick feeling at where this appeared to be headed.

“Thank you S-sir.” it was a whisper but he seemed appeased,

“That’s it, bitch.” the curse word made you flinch, and when Dean’s boots moved closer you couldn’t help but back away with your head down. Too soon your back came into contact with a freezing stone wall that felt slimy to the touch. You put a shaking hand up without looking at him, hoping he would heed your silent plea and stay back.

“Stay - stay away from me,” you squeaked when you felt his body heat on your outstretched palm.

“Oh don’t be like that,” he jeered almost playfully, but it only made your fear grow. He purposely invaded your space, stepping even closer to you until his lean frame pushed your hand back into your quivering chest. “Don’t you want to _play_ baby?”

Whimpers seemed to be riding on your every exhale, you only shook your head again finally releasing the building wetness in your eyes, you squeezed them tightly closed in response. _What is he going to do to me?_ It didn't help that your brain was supplying all kinds of answers.

_Rape, torture, murder. Take your pick._

The atmosphere between you seemed to actually thicken with his growing irritation and he moved with sudden swiftness to fist a big hand in you (h/c) hair. You yelped and squeezed your eyes closed while he bent your neck at an uncomfortable angle.

Shaking knees buckled slightly inward when you felt his hot breath right on your ear, and there was a concerning warm feeling pooling in your gut. _No no. No, nope get a hold of yourself._ This couldn’t be turning you on. Being manhandled and _threatened_ by this man. . . This very very sexy man. . _still_ there shouldn’t be tingling in your most intimate places. But there _was_.

It was making you sick.

“You answer me when I ask you a question.” a little whimper snuck past your lips at the proximity between you and it wasn’t completely born of fear, “Got it?” A long pause where you couldn’t form a single word caused Dean to practically shake with rage,

“Ye - yes. . . yes Sir.” it finally came out after a moment on a sudden sob, while you were trying to shrink away from him. His low chuckle startled your eyes open, and you took him in at his full towering height, grinning down at you with the most evil expression you’d ever seen. It made you feel like screaming.

“That’s more like it.” he murmured, seeming distracted while he studied your face. The look in his eye alone made you feel violated, and a single tear trickled out - one of many - his gaze followed it down your cheek, eyes glinting devilishly while he watched it.

Your insides felt like they were trembling.

“Don’t tell me your crying already. . .” he mocked, “is my little bitch _scared_?” Yes. God you were so scared. _So_ damn scared. . .But when you didn’t answer aloud his eyes flooded inky black, and then you _did_ scream, but it only made him smile. He gripped your jaw hard between his strong fingers and shook you a little,

“I said. . . Is my. Little. Bitch. Scared?” each word was punctuated with a painful squeeze,

“ _Yes_. . .” you sobbed up at him hopelessly, “Please, th -this is a _mistake_! I shouldn’t be here. . .” Dean pursed those full lips and narrowed his black eyes, like he was actually pondering what you said,

“A mistake, huh?” he chided, “Let me tell you something Sweetheart. . .” he leaned in and you could smell the whiskey on his breath, almost taste it on your lips. It made your eyelids heavy, “I _chose_ you.”

“Wh-what?” you whispered, clenching your fingers on the rough stone wall, and trying to fight the urge to rub your thighs together. Although your nerves were absolutely wrecked by this demon, there was still a confusing mixture of arousal and terror coursing through your veins.

_God help me._

“I chose you,” he repeated, “because I want to wake up everyday looking forward to tearing you apart. Piece by beautiful fucking piece.” to punctuate the statement, Dean suddenly smashed his lips to yours, boring his horrible black eyes into your watery (e/c) ones, and held you there for a full minute despite your struggling.

It was _nothing_ like you hoped kissing him might be. There was no movement, only still uncomfortable pressure of his warm mouth pressed so hard against yours that it made your teeth ache, while his fingers bruised your jaw. . . It was a message that your personal space, and sense of security wouldn’t be respected by him.

He broke the violent kiss with an exaggerated smack of his lips and a wolfish grin. All you could do was stare up at him with wide (e/c) eyes and an open mouth.

“Now let’s get down to business.” he pecked your nose with a sweet warm little kiss that would have been comforting in any other situation, but it now it was meant to be demeaning. And it only made you want to beg for mercy.

An embarrassingly loud yelp broke past your lips when he suddenly yanked you up by your elbow, and began dragging you toward a dimly lit hallway.

“Wh- where are we going?” you were quiet, for some reason hoping he didn’t actually hear the question, in case it pissed him off. But he flashed a dazzling smile back at you,

“Oh you’ll see babydoll, it’s gonna be so much fun.” as he towed you along it was all you could do to keep tears at bay, and try not to let your imagination loose. It was hard however, to overlook how comfortable Dean was in this environment, how much he seemed to enjoy frightening you. And that made it hard not to conclude that he was probably well versed in all things pain.

Now it seemed appropriate to beg, no amount of pride could have stopped you then anyway.

“Please. . .  _please_.” you whimpered, too afraid of him to struggle, “Don’t do this to me, just let me go - I’ll - I’ll walk out the door and you won’t hear about this again! I won’t tell _anybody_ -”

“Walk out the door, huh?” he cut you off when your voice started to rise, and you sobbed at his caviler attitude,

“ _Yes_. I promise I won’t say anything to -to _anyone_! Oh God please just let me go. . .”

“Don’t you know where you are?” the hallway was tinted red, but for the life of you, you couldn’t figure out what made the light that color. There were only burning candles illuminating the dark hall, and the flames looked orange and normal.

“No. . .” you whispered, actually allowing yourself to walk closer to him because of how unsettling your surroundings were. Like he would protect you if something jumped out of the jagged rock walls. _Yeah right._ He didn’t even glance back at you when he said,

“You’re in Hell baby.” you balked, absently pulling on his grip at the statement. "The lake of fire, Eternal Retribution, Hades. . . Whatever the fuck you want to call it.” he actually fucking chuckled about it. _Hell. Dear Lord._

“You’re lying.” you whispered hopefully, looking around at the cavernous candle lit hall,

“You wish,” and you did, “good ol' Crowley brought you down here so I can do whatever I fucking feel like without. . . well. . . killing you. You’re all mine sweetheart, for as long as I want ya.” You felt like vomiting. You felt like vomiting and then passing out in your own vomit. _Demons? Hell? All I wanted was a sad lonely night of drinking._

Tears of fear and self pity started leaking down your face, and Dean’s eyes flickered back to you when he heard you snivel,

“Aw baby, save it for the torture.” and then you were sobbing, coming so close to falling to your knees like a toddler being led out of an amusement park. Dean ignored it, easily towing you along with what seemed like superhuman strength.

When you arrived in front of stainless steel double doors, you knew it was all over. Inside the walls were white and the lighting was so bright you had to squint against it at first, but once you could see clearly you wished you couldn't see a damn thing. He abandoned you in the middle of the linoleum floor where there was a significant dip with a drain in the center, that reminded you of those old time surgical facilities.

There were other things in the room that correlated with a surgical lab theme as well. You spotted large shiny metal table that was equipped with four leather straps to bind each limb as well as divots on either side to control the blood flow into a little hole at the base.

The far wall of the room displayed every kind of weapon you’d ever heard of from basic knives to a scythe, there were also things you didn’t recognize - vials filled with colorful liquid and pointy stabby things - all sinister, all terrifying. It felt like you couldn’t breathe. Your chest ached with a breath that wouldn’t come and every fiber of your being was screaming to run. . . but there was nowhere to go.

Barely managing to tear your gaze from the wall of weapons, you found the main object of your terror. Dean currently had his back turned to you, and was slightly hunched over another smaller metal cart, you could only guess it held smaller tools like his scalpel.

They had your mind reeling.

Tears were pouring freely down your face, but you were trying to remain relatively silent like it would help if you didn’t draw attention to yourself. It was stupid, but you couldn’t form a rational thought. However no matter how hard you tried to hold it in, a tiny hiccup burst from your lips, and you brought a trembling hand to cover your mouth, watching in horror as Dean straightened and turned around.

He pinned you with a smug stare.

“What’s the matter Princess? See somethin’ scary?” he leaned forward and shook his big hands dramatically then casually moved toward you, like you were a toddler at a haunted house and not a grown woman in Hell.

Part of you wished he would actually comfort you, instead of taunting with the illusion of care. Then again he probably knew he was making everything harder for you with his sadistic games. It was sad that all you really wanted was for someone to hug you right then.

You brought your arms up over your chest and tried in vain to get a handle on your fear, he pulled his lower lip into his mouth with his tongue suggestively and popped it back out while he watched you. Every nerve was screaming to run, but you were simply too afraid.

“Yeah you won’t be needing clothes for this next part,” he grumbled not bothering to hide the way he was grating his predatory eyes over you. At least they weren’t black right then,

“Wh- _what_?” your whisper was shaky and high. _No clothes? Oh God, oh God, oh God. . ._

“You heard me. Clothes off. _Now_.” you stumbled back a few steps at the command in his voice, breathing jagged breaths,

“No. _No_!” his expression darkened again, but he didn’t advance on you yet, " _Please_. . ." he looked down on you, all hunched over protectively, with absolutely no remorse in his eyes.

“Last chance Slut,” you flinched at the name, “take em off or I take em off for you.” Sobs unleashed from your chest and your quaking knees finally buckled out from under you, dropping you to the cold smooth floor. You had been successfully reduced to a tearful mess.

“P-please don’t make me do that. .  _Please_ no -” you hiccuped on your words, and scrunched up on your knees when his brown work boots boots came into view. You put both hands up in a pleading gesture, but couldn’t bring yourself to look at him, fearing his wrath for outright defying him.

Instead of hurting you or ripping your clothes off like you expected, Dean merely squatted in front of you and waited until you looked up at him. He had a soft misleading smile on his face, which caught you a little off guard.

“Is someone afraid to be naked in front of the big bad Demon?” his eyes flickered black and watched you struggle to hold it together for a moment, “You’d do well to obey me sweetheart.” There was obvious warning in the last part, so in a shot at self preservation, you unbuttoned your shorts with horribly shaky fingers and timidly pulled your shirt over your head.

"Don't - don't touch me. ." you wept hopelessly, just praying to God this was some terrible nightmare. Of course he was gonna touch you. In fact he would do a lot more than just touch. Dean abruptly rose to stand, blatantly gripped your upper arm, and hauled you to your feet causing your shorts to drop around your ankles. You stood rigidly in front of him, only covered in your bra and panties.

"You aren't in charge here." he whispered in your face. _Yeah no shit._ You were shaking so hard you thought you might shatter.

“Dean. . Dean _please. . ._ ” you glanced up at him through your lashes and flinched at the blackness that was still in his eyes, he cocked his head to the side and raised a brow expectantly,

"What is it baby girl?" he chided, looking down on you menacingly. _Please don't rape me - please don't hurt me - please don't kill me!_  You swallowed what little pride you had left and asked your actual question,

"C-can I keep m-my underwear on?" your face reddened at the smirk on his, but he hadn't shot you down yet. What could only be described as a low growl rumbled in the big man's broad chest before he reached forward and snapped your panties against your hip, eliciting a startled whimper from you.

This could have been a dream if he wasn't so terrifying.

“I guess I can fuck your brains out during our next session. . .” you took an involuntary step back even though it was like he was talking to himself, and tried not to start sobbing again, “Yeah what the Hell. Keep em on for now, they’re sexy anyway.”  You glanced down at your black matching lace set, and felt your cheeks redden despite the fear coursing through you body. However his next command snapped you back to reality,

“Hop up on the table.” he turned away to the tool cart, expecting you to obey him, but you couldn’t move. He glanced back, “You got wax in your ears? Get on the fucking table.”

“What are you gonna do?” you swallowed thickly, feeling awkward in your own skin. He turned to face you fully then,

“You really are a stupid cunt aren’t you?” he smiled unkindly, “You’re in a torture chamber with a Demon in Hell, what do you think I’m gonna do?” you balked and sniveled,

"I -I don't want you to hurt me," you whispered pleadingly, feeling like you might cry again. What a stupid thing to say, and Dean's response let you know that he noticed too.

"No shit? I couldn't tell." Dean's sarcasm burned hot.

Swallowing your fear and ignoring common sense, you stiffly tiptoed over to the edge of the table, keeping your eyes on Dean the whole time in order to avoid seeing his array of torture instruments sitting quietly just to your left. Not a cell in your body was inclined to climb the rest of the way on. Apparently Dean knew that.

Without another warning, he wrapped his steel arms around your waist and sort of tossed you up onto the slab with a metallic clang and a frightened scream from your lips.

A big calloused hand wrapped painfully around your right wrist and slammed it down in line with the leather strap. Icy fear built as you realized that even though you were struggling in earnest, you were no match for his inhuman strength. The idea of being restrained and at his mercy was simply too much,

“ _Stop_!” you wailed, thrashing around on the table. "Nonononono!" you were bawling high pitched helpless sobs beneath him, straining hopelessly for control, and to your surprise he actually halted the buckling of your first restraint. The evil man stared at your tear stained face like he was pondering something.

“You know, we could make a game out of this.” he muttered, his eyebrow arched in a seductive manner that had your insides quaking for two _very_ different reasons. He kept one hand on your wrist and straightened up,

“Ready for the rules?”

**Notes for the Chapter:**

> Yeah. It's about to get hairy for you.
> 
> That's it for the first chapter! Let me know what you think, I love hearing from ya :) Next chapter should be up within the week.
> 
> Thanks for reading! Comment away loves ~


	2. 'And So It Goes. . .' Downhill From Here.

**Summary for the Chapter:**

> Dean introduces you to mild torture, plays some mind games, and shows you his sadistic side. It's terrifyingly wonderful.

**Notes for the Chapter:**

> Triggers for Non-Con in this chapter. Pain and Violence as well. This is just a filthy chapter to be honest :) 
> 
> Enjoy at your own risk!

Torture had always been a touchy subject for you, not that it sounded like a relaxing day in the park for anyone else, but you couldn’t stand to think about it for more than a few seconds.

In fact, once you’d had a two hour history lesson detailing the Spanish Inquisition and halfway through you actually had to make a run for the bathroom to barf up your feelings.

It was that bad.

And now you were staring at it directly in the face. _Please don’t let this be real._ With Dean smiling down at you, you tried to take a deep breath, but it pulled in choppy threatening the beginnings of another sobbing fit. You fought like Hell not to just start crying like there was no tomorrow - you had more pride than that. Dean's grip loosened minutely on your wrist, and you stared up at him with wide waiting (e/c) eyes,

“Rule number one: Don’t scream, in fact don’t make a sound, got me?” he paused while you took in the rule like he was expecting you to protest, “Number two, and this is the interesting part, I’m not gonna restrain you this time.” you waited for the catch, “because you aren’t gonna move a muscle. Not a single one. Is that clear?”

You stayed quiet, and his grip on your wrist returned to bruising, making you wince.

“Is. That. _Clear_.” he tried again,

“Yes.” you said through your teeth,

“Yes _what_ bitch?” you shut your eyes tight, squeezing another tear loose, “you better say Sir or I’ll make you call me Daddy.”

“Yes Sir.” you whimpered quickly. Dean gave a low chuckle at your sudden obedience and released your wrist,

“Arms at your sides and keep em there.” he commanded. You would never get used to the dominance in his voice, it sent shivers down your spine. With great effort you moved your shaking arms woodenly to sides, fingers scratching nervously on your underwear band because you couldn’t keep still while you just watched him scan the sharp tools on his cart.

“What do you think about starting simple?” he plucked the shiny scalpel from the cart again, and turned to you with a misleading grin plastered on his face. Reality of how serious your situation was came crashing down suddenly.

 _He’s actually gonna cut me, he has a knife and he’s gonna cut me. . . I have to stay still and silent or what. . .? Is there some kind of punishment that’s worse than being cut up?_ It scared you more to think about how versed in torture Dean obviously was, and your features naturally scrunched up with the burn of more tears, you had to close your eyes. The sound of Dean tsking made your breath hitch on a silent sob,

“Ah ah ah little girl, keep those pretty eyes open for me.” you shook your head and squeezed them tighter as tears leaked out at the image of him standing over you like a lion would it’s pray popped into your head. “The other option is me just cutting those eyelids off, is _that_ what my little bitch wants?”

“No!” you cried brokenly, “ _Nononono_. . .” you continued whipping your head back and forth on the smooth table, but timidly cracked open your eyes. Dean was smiling down at you. 

It was a taunting smile, and it told you that begging would get you nowhere. . . It might actually please him - the sick fuck - but none of facts stopped you from doing so when he raised that sparkling blade with a wink. Your resolve had completely crumbled. There was no way you could pretend to be brave through this.

“Please _don’t_. . .” you sobbed lowly, hating yourself for being so weak. You fought the urge to shrink away from him, having to grip the table to keep from shielding your body. It was next to impossible not to protect yourself. “P - please don’t cut me - don’t hurt me! You don’t have to do this. . . _Please_ Dean!” He merely raised a disapproving eyebrow at you and it took you a moment to realize your mistake,

“ _Sir_! I meant Sir. . .” you were sobbing so hard your chest felt like it was collapsing and snot had begun to run from your nose, but you couldn’t bring a hand up to wipe it. “Oh God - _please_. . .”

“Shut the fuck up.” he snarled, “No noise, or I won’t go easy on my little torture virgin.” The sinister title made you wheeze, but you somehow managed to refrain from begging some more, Dean’s warning sent yet another ocean of panic to flood your system.

“Good girl.” he purred at your silence, “Now. . . Where to start. . .” he could cut you anywhere on your exposed body, and all of the most horrible areas to be sliced open ran through your mind. You pressed your thighs together tightly, praying to God or _whoever_ the fuck could hear you that this man wasn’t as fucked up as he let on. Cold metal touched your cheek, and you stopped breathing. 

He didn’t cut, not yet, he just ran it along your soft skin and trailed it down your jaw.

While the pressure was light, you still felt the sharp bite of the scalpel's edge and it burned your skin. Dean chuckled about something, but you were too busy waiting for horrible pain that you didn’t waste brain cells figuring out what.

“So perfect. . .” he murmured. The blade traveled slowly down your neck, in between your breasts, and down the soft skin of your stomach. “I could open you up like this, see if you're just as sexy on the inside. . .” He pondered aloud, but the knife continued south until it hit the edge of your lace panties. “Or. . .” you watched him smile widely, showing off those distinct sharp canines of his. “We could go for more of a Jack The Ripper thing. . . How does that sound?”

His green irises flicked up to your face, and he looked pleased to see the sheer terror shade your expression. _No no no, oh God not that!_ Silent sobs racked your body and you used everything you had to keep quiet.

“My little slut doesn’t like that idea?” he laughed evilly, “No you’re right, I want to ruin your pretty pussy in a much _different_ way.” you whimpered. _Could I die from fear? Guess I’ll find out._

While Dean was doing a fabulous job of making you feel like pissing yourself, you found it odd though that he hadn’t cut you yet. At _all_. He was really amping it up with his dark bravado, but he hadn’t actually hurt you. . . you thought for sure that he would have reduced you to a pile of bloody flesh on the floor by now.

After a few more seconds his brow furrowed in concentration, and he stared at the blade on your skin, swallowing and shifting restlessly and you almost wanted to scream at him to just get on with it.  _Almost_.

Dean suddenly sighed heavily and pressed the scalpel more firmly to your belly, causing you to whine and struggle to keep your eyes open. Then. . . nothing happened. He was just lost in concentration for a moment before his eyes flickered up to yours,

“What the fuck are you looking at bitch?” he sneered. You only blinked at him, and his eyes flooded black with rage, and you had to look to the ceiling instead. You were past fear. . . it was all too overwhelming. A few more seconds of Dean pushing on your skin only to pull back at the last second, had you thoroughly confused. _Is this a game of some kind? Is he toying with me?_ He seemed to be getting increasingly aggravated,

“You're no different than the thousands of other souls I’ve ruined,” he growled, “you think this is a mistake? Huh? That you don’t belong down here?” the scalpel clattered to the linoleum floor, and his big calloused hand gripped one of your hips roughly.

“You think your fucking _above_  all this, is that it? With your perfect little life, and your perfect little tits. . . I bet you even have a fucking cat.” he moved into your line of sight, leaning over so his black eyes were right in your face, you cringed back a little. “ _Do_ you?” _Have a cat? Or think I'm above this. Yes to both. . .?_ Dean's voice was rising with his anger, “Answer me bitch!” he roared so loud you flinched a little, but then out of nowhere he gripped your chin and shook you,

“ _FUCK_!” he screamed so loud your hands naturally flashed up to your mouth to hold in a scream. . . You didn’t want to break his rules. But then you realized when his eyes turned green, that you had.

You broke rule number 2.

Don’t move a fucking muscle.

 _Oh God no. . ._ Dean smirked,

“Gotcha.” In the blink of an eye Dean ripped you from the table and gathered your quaking body up against him, your back to his front. Practically limp with fear, you shook violently as his big hands blatantly felt you up. He squeezed your breasts and ran a rough hand down to your panties,

“ _Stop_!” you whimpered when he grazed your core through the thin lace, his answering chuckle was chilling,

“Oh don’t worry slut, this isn’t your punishment.” his hand came down hard on your pussy with a loud smack, and you screamed in surprise. It stung and throbbed in the _strangest_ way. . . “I think you know where this is going.” he grumbled. Part of you wished he would just stop talking, because his threatening voice played a huge factor in the terror you felt.

He probably knew that. In one smooth motion, Dean sat on the metal table himself and drug you to him, forcing you over his lap without so much as a grunt. Damn that demon strength, you could never compete with that.

“What -”

“Careful. . .” Dean interrupted you, “I already have you over my knee sweetheart, don’t piss me off more.” you bit your lip, startling when he rubbed the globes of your ass through your panties.

“What did you do to deserve punishment whore?” you winced at the name, but answered.

“I - I moved without permission Sir.” Jesus your voice was shaky,

“That's right,” he muttered, “Now you get to see what happens to sluts who don't listen.” you started to cry again. It couldn’t be helped.

“Why is my baby girl crying?” there was a smile in his voice, when you didn’t answer right away he pinched your ass hard enough to make you yelp.

“I - I’m _scared_  Sir. . .” you wept, feeling so pathetic you thought it might kill you.

“Of what?” he chuckled tauntingly. _Of what??? Hell, torture, him. . . The list could go on forever._

“Of you.” you landed on that, “Please don’t hit me.” he outright laughed at you, and your cheeks reddened in humiliation,

“Oh Daddy's gonna hit you alright sweetheart.” he promised, “I’m gonna hit you until I think you’ve had enough, so get comfy.” his fingers slid into the waistband of your panties and jerked them down to your knees in one quick motion, exposing you to him in more ways than one.

In a fit of panic you bucked and struggled to grab the scrap of clothing to cover yourself back up, but his forearm held you down at the shoulders so all you could do was reach back and cover your ass with your hands. You sobbed in fear,

“Move your fucking hands!” Dean commanded so forcefully that you couldn’t defy him.

“ _Don’t_ , please don’t touch me!” bent over his knees like you were, Dean had access to more than just your ass, and that was terrifying to you, he could do whatever he wanted. The man ignored your plea and pushed his fingers firmly up along your slit. You screamed even though he didn’t enter you yet, and started thrashing around again,

“Huh. Bone dry. .” he mused inspecting his fingers while you struggled mindlessly, “I’ll have to fix that in a bit, but first you might want to hold onto somethin’, it’s gonna get intense.”  

You _heard_ the slap before you felt it, but when you did the pain was loud.

You screamed at the burning sting, only to have him bring his hand down two more times so hard your body jerked forward with the force of his hand. These were no love slaps by any means.

“That’s right scream for me bitch.” you did. He spanked you relentlessly, mercilessly, and brutally. Your tears were endless as he struck not only your ass, but the backs of your thighs, your lower back, and your pussy all with the same painful force as the last. It was never ending.

You screamed and sobbed and begged yourself hoarse. You struggled and fought and strained until your muscles gave out. Dean never tired and never slowed for what felt like _hours_ of beating you, but was probably only minutes. You were sure that his calloused hands were taking skin with them after 50 strikes or more, you didn’t even know that was possible.

Numbness is a myth, you decided, because no matter how many times he hit you, you felt every single one of them. You gripped his jeans in your fists and pressed your face into his knee even biting at the fabric, but no comfort lie there, there was no getting away from this.

Sweat coated your writhing body, and dripped from your forehead, mixing with tears, and it felt like you might vomit. Dean never relented. He counted every last blow with a smile, even laughing at your pain while he laid into you.

“Last one, you ready?” he jeered,

“ _Stopstopstopstop_. . .” that word was on repeat in your weak voice, and you felt his hand come down one last time with so much force you almost pissed yourself.

“And one hundred!” He bellowed like you had just won a little league game, “How ya feelin’ slut?” even the gentlest sweep of his hand had you tensing up and crying out brokenly, if you had any strength left it would have made you struggle. As it was, you might just pass out from the pain.

There was a distant popping sound coming from Dean’s mouth before thick wet fingers were back on your pussy again, but you didn’t have it in you to protest. You felt too battered and defeated. They were coated in his warm saliva, and he slid them up and down your entrance surprisingly tenderly.

“You look so sexy like this,” he purred, “ass cherry red for me. . raw and all mine.” you hung limply over him, unable to find the strength to move after your assault, not even when two of his fingers started putting pressure on your tight entrance. You did whimper though, frightened at the turn this was taking.

Your pussy was swollen and red from the beating, and even the slightest touches made your vision blurry with pain. He hesitated, teasing the sensitive flesh when he heard a sharp intake of breath,

“You know, I have a way to take away the pain. . .” he sounded casually mischievous, “it’s a natural remedy actually. A little something called orgasm.” you sobbed, repulsed at the thought of a demon pleasuring you.

“ _No_!” it was a scratchy cry, “Don’t do that. . . I don’t want to - to have _sex_ with you.” masculine laughter indicated that you’d jumped to conclusions,

“Presumptuous little bitch aren’t ya?” he was still chuckling, so your rejection didn’t piss him off too bad at least. “Maybe Daddy just wants to see his little slut beg on his fingers. How does that sound?” Without waiting for an answer Dean pushed his warm saliva coated fingers into your entrance, groaning at the scream that broke from your lips at his intrusion.

You could feel your walls clenching hard on his motionless fingers, trying to push him back out, it was a little painful mostly because of how long it had been since you’d had sex last. . Hey, you were a busy lady.

“Jesus you're fucking _tight_. . .” he groaned and wiggled his fingers a little bit, “maybe I will have to stick my dick in after all.”

“No stop!” with a sudden burst of energy you reached an arm back to try and claw at his hand toying with your abused pussy. Dean merely shifted and pinned both wrists behind your back with his free hand, rendering you helpless.

"I'll make you feel good if you call me Daddy," no answer from you had him ramming his fingers in hard a couple times, making you cry out, "Otherwise I can make it hurt, is that what you want? Either way I'll have fun." A frustrated shriek tore out of your raw throat when you felt him twist his fingers in and out lazily, and your horror grew when you felt how slick you had become.

The drag of his thick digits pushing and pulling almost made you moan. Almost. It actually had you biting your tongue.

“Look who’s getting wet,” there was a smile in his voice that made you want to die, but tingles and coils were wreaking havoc on your insides. _What’s wrong with me? This is so fucked up. . ._ However there was no denying the fact that your sore ass had been backburnered in your mind’s list of sensations, bringing arousal right to the front. He pulled his fingers completely out and to your swollen clit, the feeling made you buck on his lap and let out a strangled sob of sheer bliss.

“D - _Dean_!” you groaned but his fingers stilled for a moment, “Fuck Daddy, I meant Daddy!” your face reddened at his chuckle. He was winning.

“I think you should be punished for your slip up, this is Hell after all.” you gulped, fearing another spanking, “Apparently beating your ass did nothing for your manners. You close babygirl? You wanna come all over Daddy’s fingers?” To your horror you nodded your head,

“ _Yes_ Daddy,” it was automatic and you hated yourself,

“Well that’s too bad. You’re not allowed to come, at all.” he was laughing that annoying cocky laugh of his, “I get to play with this pretty pussy for as long as I want and you don’t get to come. Got it?” Jesus you were already so close, his rhythm on your clit was masterful and it was making your body jump with each pass.

“Y-yes!” you cried when he delved those wonderful fucking fingers back into your heat. “Oh God Daddy, I need. . .” there were lewd squelching noises coming from your heat as he ruthlessly pumped his rough digits into your soaking wet center. The muscles were gripping on him as you neared release,

“Sexy little cunt is _squeezing_ me baby. . . I can feel how close you are.” you were gasping and writhing on his lap, all worries lost in the ecstasy he was doling out so well. You weren’t going to last long at all, especially if that deep filthy voice of his kept telling you all about it.

“Ah. . _Ahhh_ Daddy _please_ ,” you panted wantonly and when his other hand released your wrists to move south, you knew you were done for. He spread his knees beneath you, and shoved his other hand under your hips to claim your clit roughly. You screamed in pleasure at the hard fast circles, writhing on his lap and holding his leg in a death grip.

“You better not come bitch.” he warned just as he curled his long fingers inside of you to shove them ruthlessly against your g-spot. There was no fucking way you stood a chance, and you had a feeling he knew that. 

It only took two more solid pumps before every muscle in your body clenched and you bucked back into his hand, falling hopelessly into a pit of pleasure.

“ _Ah_ \- _ah_ -” nothing really came out of your open mouth but a wordless wheeze that might have been a scream if your throat wasn’t so wrecked. Dean lazily twisted and scissored his two fingers against your aching walls as you came down, while gently rubbing your inflamed ass.

The motion reminded you that you disobeyed him, and just as soon as your body and mind touched down to reality, fear and pain weaseled back into your senses. The second he pulled his slick coated fingers from your still spasming heat you started whimpering,

“I’m sorry, I’m sorry, I’m sorry. . .” you clutched his leg and crossed your ankles, praying the more you said that word the less angry he would be.

“What did I say?” he sounded calm. Deadly calm.

“Not - not to come,” you wept fearfully, “I’m so sorry - it felt so good, I couldn’t _hold_ it! Please Dean!” he gently rubbed your lowed back,

“Shh, shh. . .” he was acting deceptively sweet and you wondered when the hammer would come down, “What happens to whores that don’t listen?” _there it is_.

“ _Please_ don’t hurt me anymore! I - I didn’t _mean_ to, oh God. . . I’m sorry!” without preamble, Dean launched your battered body from his lap with a sudden jolt and you hit the floor heavily, feeling the impact in your ribs and elbow. He towered over while you tried to scoot away and pull up your panties, but you noticed his green eyes up flick behind you to focus on something else.

“What the bloody hell is going on here?” It was that British voice - Crowley you recalled - sounding behind you and coming out rather pissed. You twisted to see, with some amount of relief, that he was addressing Dean.

You were past shame when you started crawling to the shorter man, intent on hugging his ankles when you got to him. Maybe he would save you.

“What the fuck do you want Crowley?” Dean growled his eyes flicking to black as he watched you wrap your arms around the other man's legs. Crowley acted as though he didn't even notice the contact, as if people grovelling at his feet was nothing new. Probably wasn't.

“I bring you your own personal torture toy to feed the Mark, and you bring her down here for a good wank? What kind of torture is _that_!” it wasn't looking good for you so far.

Crowley’s voice was high and incredulous, like he couldn’t believe what he walked in on. It felt like torture to you. Being forced to orgasm against your will on the fingers of Hell spawn. . And not to mention your ass felt like it was pressed up against a wood stove.

“How can the King of Hell not understand torture?” Dean countered aggressively, “You don’t just go hacking away like a caveman! You take your time, break them down mentally and physically until there is nothing left but the shell of a soul.”

_Jesus Christ he’s a sadistic son of a bitch._

“Is _that_ what you call it Dean?” Crowley sounded like he had a secret, it gave you a bad feeling about your well being. “Because from what I saw it appeared that you couldn’t make the first cut into her flesh. . . I think you might’ve had some trouble. . . Getting it up.” You spoke before you could think about it,

“No! No he um. . .” you lost some courage when both hostile stares focused on you, “he - um - he spanked me.” Your face burned red with humiliation, but Crowley listened to every quivering word with a raised brow pointed down at you.

“He. . _Spanked_ you.” it sounded like a statement. Crowley was clearly unimpressed and when you looked to Dean there was promised murder in his eyes directed at you, he looked to be shaking with rage.

_I really shouldn’t have said anything._

“Well I guess if religion preaches about Hell’s _spanking_ demons, it might scare more people into converting.” the sarcastic tone was heavy, and it was only making Dean angrier. . . It was obvious what Crowley’s ploy was and it was working.

“You wanna see a cut? Fine.” Dean stomped toward you with black eyes and hauled you up from the floor, you clung to Crowley wherever you could reach before Dean pulled you away,

"Crowley please don't let him!" you bawled, "Help!" he only gave you a small melancholy smile as Dean hauled you off. So much for the kind Scottish man at the bar. You wanted to throw up.

“Come here bitch. You’re gonna learn to keep your fucking mouth shut.” you screamed and jerked on him while he drug you to the table again,

“Dean no, don’t!” you cried, but it fell on deaf ears and you were slammed face down on the table so hard it chased your breath away. Dean was quick in securing the straps around your wrists, mostly due to the fact that you were too terrified to struggle with him. He didn’t bother with the ankle straps before he snagged the scalpel from the rolling cart once more.

“Screaming is allowed this time.” he snarled the sentiment in your ear before pushing the sharp point into your left shoulder blade. You _did_ scream. You screamed so loud and for so long that you tasted blood in your throat.

The pain was so intense that you couldn’t even cry, and it felt like he was at it forever. He was drawing something specific on your back. Blood rolled into your armpit and down your back, staining your underwear dark sticky red. 

Dean was speaking as he worked, but you couldn’t focus on what he was saying, only bits made it to your brain.

“Stupid cunt. . . make you mine. . . belong to me forever. . .” none of it sounded good. Finally, fucking _finally_ the blade was pulled from your back and he turned his back on you to throw his hands out to Crowley,

“That good enough for her first day?” he spit. Through your tears you saw the King of Hell smirk slightly,

“D.W. hmm. . . as in Dean Winchester?” he was smiling widely, “If I didn’t know better I’d say this particular tart’s got a hold on you.” Dean rumbled with an angry growl, and Crowley cocked a brow at him before giving you a tiny wave,

“Until next time my dear.” and with a snap he was gone. Your vision was blurry from the pain of having his initials carved into your shoulder, but you could see that Dean was still pissed when he turned back to you on the table. He jerked you back by your hair and snarled in your face,

“You ready for your real punishment for coming without permission?” you couldn’t even scream there was so much pain shooting steadily through your body.

“No. . . No more Dean. I can't take it. .” he laughed in your face, his hot breath hitting your mouth, the next words were not spoken kindly.

“No sweetheart, not Dean. You only call me Master.” bile rose in your throat at the thought. _I can’t call him that. . . No God no. . ._ He didn’t seem to care that you didn’t respond for now though.

Through your daze you still flinched when his hand closed around your right ankle, but you had no strength to fight when he jerked your legs open and secured them to each ankle strap. The cold air of the big room hit your pussy, still slick with your orgasm. The feeling of being splayed wide and vulnerable to his every desire or touch ignited panic within you once again,

“Wh - what are you doing?” the question echoed slightly, and not being able to see Dean made you uneasy. There was no answer, only roaring silence. Until you felt his fingers on your cunt again. “ _Don’t_!” you screeched, pulling uselessly on your restraints.

Again he ignored you and spread your lips with two fingers, the anticipation was the worst part and Dean was milking it. After a few heavy moments there was a slight pressure over your clit that made you jump, and then an intense pinch that lingered for a moment and faded.

You yelped loudly and he withdrew his fingers, but there was still something pressing on your clit.

“What is _that_!” you yelled, feeling your eyes mist over. Never before had you felt so helpless and threatened, and these were feelings that you would never get used to. This time Dean did answer you. He waltzed back into view with a tiny remote in his hand and a shit eating grin on his face.

His eyes were still black, apparently his anger didn’t dissipate very quickly. The fear in your (e/c) eyes must have been clear as day, and there was no doubt he could see you shaking. Those horrible black orbs glinted dangerously,

“Oh don’t worry slut, you’ll like this. . . At first.” he chuckled, then took on a concerned facade, “What’s the matter babygirl? Don’t you trust me?” He was toying with you like a lion would a mouse, you would say a cat but he was much more ferocious. You choked on a sob and closed your eyes, fearing the worst.

“Would it make you feel better if I counted to three?” you did start sobbing then - why bother hiding it anymore - he chuckled at your weakness. “One. . .” he leered evilly,

“Please just stop!” you wailed, tired of hurting.

“Two. . .” you wept miserably, “Three!”

Every muscle tensed just before you heard the click of his remote controller. Strong vibrations overtook your clit and made you scream at the sudden sensory overload. Your eyes flew open to look at him, he was drinking in every detail of your shuddering body like he wanted to eat you alive.

The vibration was so intense it was almost painful on your already sensitive pussy, but there was no denying it was bringing you to climax at an alarming rate. Dean started speaking,

“This _would_ be a standard clitoral vibrating clamp. . .” he spoke slowly studying you, and you knew there was going to be a catch to all of this. He did say it was punishment after all. 

The pleasure precipice was hurtling toward you quickly,

“Except that. . .” you moaned and stiffened feeling your orgasm about to wash over you, and you craved it - oh _God_ you needed it. The other plus was that this climax wouldn’t be at the _hands_ of a demon and somehow that made it a little more tolerable for you.

Your breath hitched just as your pussy began to spasm with overwhelming relief. . . and then the vibrations stopped. Your eyes snapped open wildly and found Dean staring down at your expression with the most sadistic evil fucking smile a man could wear,

“Except that as soon as you're about to come, it turns off all stimuli.” _Oh fuck no. Fuck no_. “Courtesy of Hell, this is gonna be fun. Well for me.”

Out of nowhere the vibrating started up again and you shrieked and struggled with the tethers at your ankles but all it did was heighten your suffering. You lifted your ass trying to find friction to send you into orgasm but it was crushingly useless.

Tears were steadily flowing when the pulsing stopped again,

“Oh _sweetie_. . .” Dean mocked, “that was only your second surge, I'm gonna fucking break you.” 

“Fucking make it stop! Just untie me you son of a bitch!” sexual frustration was making it hard to remember to fear the powerful demon,

“Nah. . I think I’ll leave you like this for a while,” he mused dramatically, “maybe if you're a good little bitch I’ll let you come for breakfast. That’s in about, _oh_ , eight hours.” You gasped and on cue another surge started up on your throbbing clit,

“ _Ah_!” Dean was turning away from you, humming as he strode toward the door, as what appeared to be an afterthought he glanced back at your writhing body with a devilish smirk,

“Sleep tight princess.” again the vibration stopped, and you collapsed against the table that was already sticky with sweat and embarrassing amounts of arousal pouring from your opening.

_This is gonna be a long fucking night._

**Notes for the Chapter:**

> From here things start to get a little more defined - relationship wise - between reader and Dean. Still smutty and all, but it develops more.
> 
> Comments! I love them all :)
> 
> ~Hope you enjoyed~


	3. Break Her

**Summary for the Chapter:**

> Dean continues his sadistic game with you. . . but something seems off about the demon. Will you survive to figure out what it is?

**Notes for the Chapter:**

> Whoa. Long wait. . So sorry, I just needed extra time on this one. There was a lot of deleting and re-writing involved. Anyway I hope it's worth the wait, and thanks for sticking with me! :)
> 
> This chapter has a lot of humiliation and emotional torture/manipulation. . . Also the end of this chapter gives me goosebumps so prepare for that crap. :)
> 
> Enjoy~

Sweat slicked the metal slab he’d left you on.

There was so much pain that you weren’t even sure you were a person anymore, so exhausted that you’d lost the ability to even react to the torturous vibrating surges long ago. You had stopped counting at 23, it was impossible to even think clearly after that.

Time didn’t exist anymore. Only tears and pain, pain from the ruthless piece of metal attached to your swollen clit, pain from your muscles that couldn’t stop tensing and the beating you’d taken, and pain from the initials carved in your back that reminded you who left you like this. The idea that you could die via edging might have made you laugh if it didn’t feel like it was actually possible at this point.

Plus your nipples were sticking to the damp metal which, granted, was the least of your concerns but still all sorts of irritating, the least he could have done was left you on your back. What had to have been the 200th surge took up massaging your panicking clit, and had you arching your hips back off of the table with a low sobbing groan.

It was never ending.

In the beginning you screamed in anger, cursed Dean’s name for all of Hell to hear. After a while the anger turned into desperate begging for someone to make it stop, but after hours of going unanswered you lost the energy to keep trying. Now it was occasional crying, a scream here and there, and gargled moans that you didn’t even think a human could make before this.

The vibrations took your desperate body back to the edge again, making you pant face down into the sticky table, only to cut off right at the brink like all of the times before. You cried out brokenly, sobbing like a woman who just lost her child.

This was too much.

Steady dripping on the floor taunted you with how wet you had become, it was basically pouring out of your pussy and running slowly down the table to the tile a few feet down. Your wrists and ankles were raw from the leather restraints, from hours of pulling and struggling to touch yourself, or rub your clit on the table. . . _anything_ _to make this pressure stop._

Once throughout the night, you had come worryingly close to throwing up all over yourself, elevated body temp and continuous strain will do that to a girl. That fucking click happened again and the simulation was back full force, only having given you that minute to calm down a little before it was back to torturing you.

Sometimes it would take a long time to get to the edge and those ones were the worst.

In the middle of this surge you started to whine so loud that you barely heard the metal doors swing open, you didn’t even have the consciousness to turn your head at the noise. A choked bleat oozed from your lungs and the vibration cut out, leaving you to collapse back onto the slab like a bag of water.

“Well ain’t that a pretty sight.” just the sound of his voice made you whimper. If you didn’t know it before, you did now. . this guy was a fucking monster. You heard him leisurely waltz up to your shoulder, but still didn’t waste the energy to look at him, “You know even after I came in here about an hour in to watch you scream and cry. . it still hasn’t gotten old. I know I said eight hours, but damn baby, I could watch for another day. Hows that sound?”

It was stupid to think you ran out of tears, because at this suggestion you were back to sobbing hopelessly and wishing for death. The knowledge that he’d watched you endure some of this, silently and without a care in the world made your blood boil. As soon as you found your voice another surge started, and you wailed briefly, trying to speak through the over stimulation and your sobbing,

“Pl - _pleeease_ make it st - _stop_! Oh pleeease please _please_. . .” your body jerked involuntarily as the clamp buzzed on, “A -ah! Ah can’t t -take it. . . _hurts_!” you stretched the restraints as you neared release only to thrash around when it stopped again. You didn’t know whether you wanted to come or die.

“Aw my little slut is so polite when she’s being tortured, I’ll keep that in mind for the future.” he mused as if there wasn’t a suffering naked woman strapped down in front of him, “You wanna come sweetheart?” at his words the vibrations started again and you screamed,

“ _Yes_! Yes please make it stop!” silly you really thought he was gonna let you ride it out this time, so when the stimulation faded away a flash of red anger snapped in your brain,

“Too bad, maybe next time.” he chuckled carelessly. Then you did turn your head to look at him, he was looking down at you with the most smug expression on his stupidly gorgeous face,

“I hate you, you fucking monster! You god damned evil son of a bitch! I fucking _hate_ you! I’ll kill you with my bare hands if I - _AHHH_!” more vibrating cut off your rant, and Dean laughed so genuinely that he leaned back into it before bending forward and bracing his hands on his knees while you writhed and struggled in agony. The buzzing died before his laughter did.

When he recovered from his laugh attack he rose and patted your raw red ass a little too firmly,

“Looks like all I gotta do is edge you a few hundred times to bring out that fighting spirit,” he was still chuckling, and your watering eyes followed him as he walked down the table, “Good to know.” Dean was scanning your sweat soaked twitching body curiously, emerald eyes roving to your core where his eyebrow rose in what appeared to be appreciation, until he was between your feet and out of view.

That made you nervous,

“What are you doing?” you growled, jerking on the leather, “Don’t fucking touch me!” the smile in his voice was audible,

“You sure about that babe? Cause from the view I got down here, that little pussy of yours is just _beggin_ ’ to be touched.” the wetness of your sex was chilled by the temperature in the vast room, leaving permanent goosebumps along your body, it was such a strange and uncomfortable mixture of hot and cold down there.

You hated that he was right, that he knew what you needed, but there wasn’t a atom in your body that was gonna ask for it. Or admit it. Not even after all of this suffering.

Another surge hit, making your sex clench and gush before his eyes, and you thought you might have heard a sharp inhale from the demon but you were too busy dying of humiliation and intimate pain to speculate. However when warm breath hit your cold wetness you mewled loudly in confused protest.

_He isn’t gonna. . . is he?_

You glanced back to find him hedging back over to your side with his face hovering just above the apex of your thighs the whole time he was sidestepping. His eyes were black, his mouth hanging open, the visual of this ruthless demon zeroed in on your most sensitive part made you shiver, it was frightening to say the least.

 _What is he gonna do?_ Surely not what a normal man might do in this position. . . not what you secretly craved in this stage of orgasm deprivation. . . No he was gonna tease you more. Maybe hurt you. But surely not -

“ _Ahh_!” you screamed in both surprise and nervous pleasure when his tongue snaked out and lapped once right smack at your opening, collecting what had to be a river of slick with the soft velvet spear. _Oh God he fucking did it._ “W- what are you _doing_?!” your voice embodied a terrified woman, it was shrill and shaky and there was no controlling it anymore. He didn’t look away from your dripping center when he spoke,

“Could’ve sworn you said you wanted to come sweetheart. . .” he drawled, slowly tracing a finger up the back of your trembling thigh. You sobbed,

“I _do_. . .” the admission stung, “b-but please don’t do that. . .” he did look at you then, a little surprise sneaking into his black eyed features,

“Do what baby girl? Lick you?” he chuckled at the fear on your face, “I just wanna taste you sweetheart. . . I get a taste of what’s mine, and you get to come. Everyone wins here.” _His_.

“No, don’t touch me!” you jerked on the restraints again, even after everything the idea of letting him get that intimate with you was horrifying. There was no trust there, he could bite your clit off for all you knew, and for God’s sake, you were a mess down there. Dean clicked his tongue and shook his head,

“Mmmm, I think you taste too good to pass up.” he mused dramatically, as if there was any chance he wasn’t going to do what you were begging him not to.

“No! Please don’t, not _that_. . . _please_ not that.” you squeezed your eyes closed and felt his breath on your ass again, making you whine brokenly and tense everywhere.

“What makes you think you get a say?” then the vibrations started up again and you wailed, but not a half a second in, Dean’s hot mouth was latched onto your aching and chilled core. It was almost soothing how he slowly ate you. The feel of his hungry tongue invading your swollen lips made you jump off the table, and coupled with the vibrator it was a feeling akin to ecstasy.

Your morals were lost as quickly as you were. He was being gentle, which was odd, licking just barely into your opening and growling at the taste. It was like a firm massage really, and it had you groaning. His warm soft tongue gave you shivers as it just barely met the antagonizing clamp on your clit and he gave it a little nudge just to hear you scream.

His evil smile formed so obviously on your delicate skin just before it all stopped once again, including his feast.

“ _No_! No, no, no _fuck_!” you cried, “I hate you, you horrible son of a bitch, I fucking hate you!” he was laughing,

“You change your tune pretty quick there baby, so what is it that you want?” he clapped a hand down on your sore ass and left it there like he was leaning on a counter,

“Let me come, _please_ let me come. . .” you wept, trying to wipe your nose on your shoulder,

“How?” oh so this is what he wanted. After a moment of trying to force the words, you told him quietly,

“I can’t say it.” he pursed his swollen lips and pretended to be confused for a second,

“Ah. You want me to eat you out. . Is that it?” he was grinning like mad and you had to look away from that scary black eyed stare. His sharp sparkling white teeth contrasted jarringly with his eyes. . It reminded you of a shark, but somehow more dangerous, and even though you didn’t answer his breath ghosted across your ass and you locked up ready for anything - shaking violently. You were terrified.

Another beat passed where nothing happened, and you were just tight as a bow waiting for violation or pain. When he spoke his voice was different, deeper and softer somehow - almost kind,

“Calm down. . . I won’t hurt you right now sweetheart.” you sobbed at that little mercy, but didn’t totally believe him.

“Please. . . please. . . _please_ ,” you begged fearfully, hoping to God that he was telling the truth, because if he wasn’t there wasn’t a thing you could do about it. This time he leaned partially across the table for better access to your desperate pussy. Threatened whimpers were escaping still and he brushed a hand down your lower back sort of tenderly,

“Relax for me.” as soon as the clamp buzzed he lowered his mouth again and got to work. The feeling made your head throw back with a broken cry, and you tried to push your hips up to meet his mouth more solidly.

Rough hands grabbed at your hips and lifted for you, and upon looking back, you saw that he was basically on the table with you, laving and growling like a man starved. His black eyes were trained on yours while he licked and occasionally sucked at your lips. . . the whole thing was just obscene. . . and sexy. It was incredibly sexy to have this black eyed knight of Hell eating you out with abandon while a vibrating clamp massaged your tortured clit mercilessly.

The image and _idea_ had you back on that beautifully horrible edge yet again, and it was like your whole body began to vibrate.

Suddenly Dean shoved his tongue deep and began doing this thrusting and curling thing that had you seeing stars and begging him to never stop. Even the way his teeth scraped around lightly as he tongue fucked you was pleasing instead of disconcerting. Then with a wink Dean used his thumb to press down on the vibrator to grind it with your clit and you came.

 _Finally_.

It was violent really, the way you jerked and writhed around, screaming and sobbing as wave after wave of orgasmic bliss crashed from your pussy. The clamp buzzed on and Dean licked and licked inside of you until you were only a panting mess, occasionally jerking at the aftershocks.

Honestly it felt a little like you might be sick all over yourself, but you just laid quietly shuddering as Dean finally removed the clamp. Blood rushing back to your clit made you whimper and to your surprise Dean again responded gently,

“Shh, _shh_ , here let me. .” and his tongue was flat and soft against your abused bundle of nerves, just gently massaging it up and down until it didn’t feel so painful anymore. When you started to relax again, he moved up along your slit, cleaning the lingering wetness off of your quivering lips somewhat greedily. You moaned and sighed in response to his warm gentle caresses, hoping he would continue to be kind.

Praying really.

“How was that babe?” this sudden change in him was unnerving, but you preferred it greatly over sadistic demon Dean so you said,

“Thank you sir.” and actually meant it, because _fuck_. . that unbearable pressure was finally gone, leaving only an uncomfortable tingling behind. Dean grunted in acknowledgement and dismounted from the table smoothly, dropping to the floor with a thud from his work boots.

When his rough hand suddenly grabbed your wrist you jerked and whimpered, face screwing up with fear - after all there was no telling what this man would do. Again however, he responded with kindness.

“Hey, you’re alright baby girl,” with your eyes closed tight, you felt his lips press against your temple as he worked on the restraints, “I’m just getting ya out of these. You feel like you can sit up for me?” you were shocked silent.  _What the Hell is going on. . .? Why isn’t he taunting me, or - or hurting me. . .? It has to be a game. Right?_ So you decided to test the waters,

“Everything hurts. . .” you sounded pathetic, no voice anymore really, but it wasn’t a lie. You were in all kinds of pain. Dean chuckled down by your feet while he unfastened your ankles, but it wasn’t a condescending sound like normal, it was more of a nod to you, like he was saying _“I hear ya.”_ without any words at all.

“Well not _everything_ hurts. . . Could be a lot worse.” finally you were free, but you didn’t dare move yet. He was right, it could be worse.

Dean had already said that down here in Hell he could do anything he wanted to you, and you would never die. . . So realistically, you could be strips of hanging from hooks instead of just a whole girl, who was fucked out and exhausted. You shuddered.

“Go ahead,” he rumbled, “sit up.” you swallowed, taking note that your ass was still basically raw from his earlier beating.

“I - I can’t move sir,” you sniveled, only to cry out in a second when his hand sharply swatted your ass,

“I said sit up.” he growled, and you did so with pained grunts and stiff movements. God you just wanted to sleep for five years.

“Sorry,” it was soft and it almost hurt to say, but there was nothing you wanted more than for him to continue with this new caring Dean. He looked a little surprised at your voluntary apology for a moment before putting an indifferent mask back on and nodding once. Once you were properly seated, putting most of your weight on your hands beside your thighs.

His hands were suddenly on you, gripping your waist hard enough to bruise, and in a panic, you struggled and screamed. One hand left your waist to wrap around your back, and before you knew what was happening he laid a palm over his initials. The were still slowly oozing blood, likely festering, and burned like the fires of a thousand suns. So what you did next was purely out of need to get away from that hand.

You flung yourself at him and wrapped your arms around his waist, sobbing into his chest.

"No please, it hurts - _please_!" you bawled, "It hurts, it hurts, it _hurts_. . . _please_. . ." you just kept babbling into his shirt, but he held the pressure on. _Why wouldn't he? Hello, demon in Hell here._ Dean pressed down harder and you screamed at the burning sensation, " _Ow_! Stop, oh God stop!" but suddenly all of the pain was gone. The intense fiery agony only a fresh memory.

"What. . .?" you rolled your shoulder like it would come back, but it didn't, so you looked up to Dean - whom you were still latched onto - questioningly.

"I healed it." he stated simply, "It's just a scar now." you only gaped so he just explained further, "When Angel's heal you don't feel a thing, but when Demons do it, it burns like a son of a bitch. Hence the reason you acted like a four year old just now." you straightened at the barb, and detached yourself from the well built man. Yeah you noticed how hard his muscles were just now for sure.

"Um. . . Th -thank you." you looked to the floor, but couldn't deny that you actually meant the words. _Why would he heal me? Doesn't he want me to hurt?_  Dean only winked and said simply,

“Now it’s your turn to eat something slut.” you flinched at the sudden name calling, but it wasn’t said harshly so you let it slide. Like you could do anything about it anyway.

However his words sent a jolt of apprehension through you, and you stiffened on the metal slab - a quick glance to his jean covered crotch revealed that he was in fact hard at the moment, and you couldn’t help but think Dean was about to force you to blow him.

A tear fell out and you whimpered quietly, looking to your clenched thighs.

“What’s the matter pet? Aren’t you hungry?” he sounded amused, “You must be hungry by now. . .” the worst part - well not the worst part - but another terrible fact was that you actually _were_ hungry. For food. Not. . . _that_.

When his big hand came to rest gently on your knee, a few involuntary frightened noises shrilled through your lips, and you sniveled, clenching your thighs even tighter. Feeling vulnerable was a horrid thing when you were with a demon.

“P -please don’t make me do that. . .” you whispered almost inaudibly, and he leaned in closer to hear,

“What was that?” as if he was actually interested in what you had to say,

“Please don’t make me. . . do that.” you repeated a little louder but no less shaky.

“Do what?” and you had to look up at the confused note in his voice, his face matched it. “Eat breakfast?” you just stared at him with your mouth slightly agape unsure now what was going on. Clattering outside the metal doors caught your attention, and a couple seconds passed before two men burst in with a rolling cart. There were serving trays on it.

 _He really meant eat food. Oh God. . ._ Your face burned, and as if that was all Dean needed to understand what you had assumed, his pretty face cracked into a huge grin.

“Shit baby, you got a dirtier mind than me.” he gave your thigh a slap that made you jump and turned to the newcomers who looked to be awaiting orders. Dean waved a hand noncommittally at them, “Get the fuck outta here,” and with bowed heads and hasty movements the two bumbled out as fast as they could.

_Jeez, even other demons are afraid of him. . who is this guy?_

“Not that it isn’t comin’ soon enough,” he continued casually as he uncovered some trays and studied the contents, “just not now. . . I need you to eat to keep up your strength. It’s no fun when you don’t fight me a little.” you swallowed, staring blatantly at him with huge widened (e/c) eyes and he held it for a moment before he turned back to the food, “

Besides, wouldn’t want ya gettin’ too skinny, I’d say you’re just perfect right now. .” he glanced at you, “I’d be some kinda dipshit to mess that up.” despite it all the compliment made you swell a little, so you quickly reminded yourself how wrong this all was.

But God. . . he was attractive to say the least. . and this whole nice guy routine was confusing your brain - and insides - plus. . _I mean the guy just had his head between my thighs for fuck’s sake._

The demon plucked a tray from the cart and moved back to you, uncovering it to reveal at plate of eggs, bacon, sausage links, buttered toast, and strawberries. Your mouth watered. Oh _God_ were you hungry. . . In fact at the heavenly smell of bacon your stomach roared with demand, loud enough for Dean to hear. He smirked while your face flamed.

“Go ahead sweetheart,” he nodded with a devilish grin, but you were too ravenous to care about a potential trap or poison or anything really. So ignoring his piercing gaze, you reached for a strip of bacon, only to have Dean swat your hand away with a quick stinging precision.

“Ow -!” you yelped and scrambled back on the table, peering at him with pathetically frightened (e/c)s.

“Aw baby you’re breakin’ my heart with that beat puppy look,” he jeered with a chuckle, “why don’t you just ask for some help?” the demon watched you try to work out the riddle, and must’ve seen when the light bulb went off, because he huffed a laugh at your uncertain expression.

“You know. . .” he started, picking up a piece of sausage and biting into it, “they even brought a can of whipped cream in here, if you're good I might eat you again for dessert.” you gulped audibly, feeling your face redden at his crass words. You sniveled and shook your head nervously, “Oh fine, _fine_. . . touchy jeez.” he griped, “Are you hungry baby girl?”

“Y- _yes_.” you wiped a tear away, trying to keep from curling up and crying until you died.

“Then _ask_. For. Help.” he popped the rest of the sausage in his mouth, making a show of how good it tasted. _I have to do this. I’ll do this to survive._

“W-will you. . .” he quirked a brow expectantly, “will you feed me sir?” _kill me now._

“Of course sweetheart.” and without delay he picked up the bacon you went for earlier and held it at the edge of the table. _Okay count me as surprised. . . He's actually gonna do it? No games?_ Timidly you scooted back to the edge of the table and stretched your neck to take a bite. He let you. Even holding it up while you chewed for another bite,

“There we go. .” he praised, “wasn’t so hard was it?” Dean continued hand feeding you bacon, sausage, toast, and strawberries. The eggs however, he seemed to be saving for last. In the end it was clear why. In order to eat the eggs properly, you had to basically put your mouth over his fingers and pull them off. . . it looked obscenely like you were doing. . something _else_.

Your face burned, and that shit eating grin on his didn’t help your embarrassment at all, but when the plate was finally clean you realized things could always get worse. Dean said,

“Good now lick my hand clean slut.” he held his palm out, and you only hesitated for a moment before shutting your eyes and getting to work. _At least he isn’t hurting me, at least he isn’t hurting me. . ._ That was your mantra.

It took way too long for him to take his hand back, Dean was obviously enjoying this little show more than he should, but when he finally did you held your eyes closed in shame. _If momma could see me now. . ._ Dean clapped his hands together, startling them back open.

“Alright. Shower time sweetheart, you’re gorgeous, but you smell disgusting.” _ouch. Alright he’s still an asshole then._ However you couldn’t argue that you smelled less like flowers and more like a sweaty mess, so you nodded at him timidly.

“Come on, you can shower in my room.” you came off the table when you grabbed your hand, but balked a little, “With me.” at that you dug your heels in. Dean only acknowledged your struggles when he was almost at the door with you, and he turned around with a raised brow, looking like a parent about to reprimand a misbehaving child.

“Careful girl. . . you’re making me angry.” there was an edge to his voice that made you stop struggling and huff in desperation, looking around the big room like something would help you reason with the demon. _Stupid_. Dean had a little amused smile on his face, eyes shining in wait for you to say something. So you did.

“I - I’m not showering with you.” Oooh, wrong thing to say if his now-black eyes told you anything. Your body automatically tried to jump back from him, but he was still gripping your arm.

“Excuse me?” he jerked you forward and you crashed into his chest with a tiny cry, he didn’t let you pull back, instead you had to look directly upward into his face. You lower lip was trembling and your eyes became bright with frightened tears, although they didn’t fall yet.

“I’m sorry sir,” you whimpered up at him, but his anger didn’t falter, “I - I don’t want to take a shower with you, please don’t make me.” Dean was vibrating, his hand tightening on your arm, but you didn’t dare squirm,

“I fucking ate you out, let you come, fed you, healed your cut. . .” he was speaking through his teeth, “and I ask you to do _one_ thing - to take a fucking shower - and you _can’t_?” _well when he put it that way. . ._

“I j -just don’t want you to touch me. . .” you had to look away from his eyes, jumping when he snorted,

“Don’t want me to _touch_ you, huh?” it sounded like a statement, all you could do was trembled against him, “Fine, I won’t touch you sweetheart.” you were thrown to the hard tile floor, crying out when your elbow smacked down first and barely scooting away from the angry demon.

“I -I’m s -”

“You’re _sorry_ , yeah I heard.” he snapped, not even glancing at you when you couldn’t hold a dry sob in. Dean stomped over to a cabinet along the wall and with his back still turned beckoned you over with two fingers. He was already pissed enough, no sense in making it worse on yourself, right? So you started to stand,

“No. Crawl.” he growled, again still not looking. Taking a deep breath and swallowing thickly, you shakily began to crawl to him with your head down. It was likely that you didn’t want to see all the things in that cabinet anyway.

When you were within arms length, what could only be described as a shackle was snapped around your neck. You fell back, flailing and yelling at the abruptness of it all. . . and your hands went to it, feeling nervously like there was going to be some secret razor hiding within, like some “Saw” movie device. It was thick iron and connected to a chain that Dean was holding.

Just a simple collar and leash after all. Demeaning and scary, but not causing pain at least at the moment. He watched you fret over it for a second or two, before moving to the connecting wall and threading the chain through a hanging loop.

“You might wanna crawl over here, or I’ll just drag ya.” he sounded bored almost as you did just that. He pulled the chain through until you were standing against the wall on your tiptoes next to him. Then he gave you this black eyed look that chilled you to the bone before his eyes went green again,

“You know how easily I could just -” he jerked the chain and cut off your air momentarily. You flailed and grabbed at him for the few seconds before he gave some slack, “ _Kill_ you right now?” he finished while you sucked in choppy precious breath, then he grabbed your face, “Don’t you fucking forget it bitch.” with that he let go with a shove to the wall, and hooked the end of the chain to the floor so you couldn’t move from the loop.

_Oh no this isn’t looking good._

“You said you didn’t want me to touch you right?” he walked back to the cabinet with his lips pursed, and you finally let the tears spill over, wishing more than anything that you would have just let him fuck you in the shower. If that’s even what he was going to do that is.

“ _Please_ sir I didn’t mean it, I’m so sorry.” you wept, clearly not getting through to him. It was like he didn’t even hear you, “I’ll - I’ll shower with you, I _will_ \- please don’t hurt me! I’m sorry master _please_!” he perked up at that, and you stared at him completely shocked that you’d actually said it. _I called him master. Oh God._

“Hmmm. . .” he chuckled, “Looks like you're learning quick sweetheart, I guess fear really is the way to go with you.” he pondered you for a moment, before turning back to the cabinet, “But you still need a shower, so shut the fuck up while I give you one.” _what_? Dean pulled a heavy duty white fabric hose.

_A fucking fire hose._

“There we go.” you saw him roughly twist what had to be some kind of source of water inside the cabinet, before the hose began to fill with pressure.

“No! No don’t do this!” you started jerking on the shackle around your neck, and uselessly pulling on the metal ring, “Dean don’t, please!” but he was grinning, leisurely waltzing closer with the nozzle lazily aimed at you.

“What’s the matter baby?” he laughed, “You said you didn’t want me to touch you.” if the collar wasn’t already putting tension on your neck, you would have slid to the floor. Dean twisted the valve on the hose and water started shooting out at such a velocity that when it did hit you, there would be pain.

The water was pelting the floor right in front of your feet, and you pressed against the wall shaking your head and weeping. _Why did I have to tell him no?_ With a wink the water was on you. It was cold, that was the first thing you noticed, was that it was like ice water on your skin. However it didn’t take long for the feeling of a million needles flying at you per second to get you to start screaming. You tried to turn around only to be yelled at,

“Hey! Front facing me, don’t make me tell you again.” he was laughing as he shot every inch of your front with the high pressured hose, and you were sobbing as the water beat down on you relentlessly. He took the spray off suddenly. You were shivering so hard your teeth were chattering, your skin was bright red from the freezing pinpricks. Then he said something that made you want to die,

“Turn around and bend over.” you stopped breathing. Dean had a humored smirk on his face that made his green eyes crinkle in the corners. Knowing that this was about to be the most humiliating thing that had ever happened to you, you turned, breathing harsh while he moved to loosen the chain on the wall. You hesitated with the second part.

“Don’t make me say it again bitch, bend over.” with tears flooding your cheeks, you did ask he told you, touching the floor with your fingertips. Dean was right behind you suddenly and you shot up at the feeling of his hand on your ass. “Ah, ah babe.” he slammed you back down by the neck, holding the pressure there while he kicked your feet apart with one of his booted ones,

“No, no please don’t!” you begged loudly, thinking he was about to rape you like that. “Please Dean, _please_. .” sobbing, you brought your hands back between your legs to cover your exposed sex, “ _Please_ don’t rape me!”

“Can it.” he snarled venomously, finally releasing your neck to bat your hands away. You stayed down, crying. “Good girl. Stay just like that and you won’t get hurt.” of course you didn’t believe him. _Who would?_ He didn’t exactly say he wasn’t about to fuck you either so you stayed tensed for anything.

The hose turned on. You screamed before he even did anything, but when the icy water touched your pussy, it wasn’t as high powered as last time. Still pressurized and forceful, but it was definitely creating a feeling other than pain.

 _Oh sweet Jesus no. . .yes. . ._ He moved the water up to your asshole, making you jump and cry out while he chuckled at your endless reactions. Dean did this for a long time, moving the spray up and down, up and down, until you could feel familiar tingling over the numbness that the cold created. You were gonna orgasm like this was a bathroom shower head.

Before you could stop yourself, your hands were palms down on the tile so you could push your ass out more while you inched your legs wider for the stimulating spray.

“Oh. . . _oooh_. . .” you moaned involuntarily, opening your eyes to see the culprit of your immoral pleasure crouching while one hand lazily worked the hose. He had this strange look on his face, a mixture of pleased and patient that seemed unnatural on his naughty features.

In the end though he gave you what you wanted, and turned up the spray a fraction before focusing directly on your clit.

“Ahh!” you cried out, canting backward for it and even reaching back to spread your lips so the water would hit it more,

“Damn baby. .” Dean rumbled at the show, winking when you cracked an eye open again to look at him. Two seconds passed before the water sent you into a jerking spasming orgasm. The force of your pleasure brought you forward to your knees, and you had to slam your legs closed against the following hose.

You laid trembling and jumping, both from the cold and your lingering climax, as Dean heaved himself up with a grunt,

“Would’ve been so much better in the shower though sweetheart,” he pet your head while you hugged yourself, hating that he so easily took control of you like that, “next time you won’t say no.” he sounded sure of it, and as much as that should have pissed you off, he was probably right.

“Now.” he squatted in front of you and gripped the chain right at the base of your neck, “Kiss me.” he commanded with a glint in his greens.

“W -what?” your voice was hoarse from screaming and sobbing,

“You heard me sweetheart, lean in and give me a little kiss.” he was smiling like this was hilarious, like he was expecting you to refuse so he could punish you more, but you vaulted up onto your knees and slammed your freezing lips to his full pink ones. Dean gave an “ _ooff_ ” of surprise, but immediately kissed you back.

It wasn’t that you _wanted_ to really, it was just that kissing this impressively attractive man over torture seemed like the most simple decision in the world. You’d be a fool not to do it. At least that’s what you were telling yourself as you moaned when he introduced his tongue.

 _What’s happening to me?_ The thought coupled with the fact that he suddenly grabbed a breast, made you pull away suddenly, causing the demon to grunt at the loss. Dean watched you cower back into the wall and cover your chest with your hands, licking his lips clean of the taste of you, and then he sighed, eyes flooding black.

“We could have gone so smoothly from here, but you have to keep fighting. . Now the fun really starts.” you tried to scramble back when he extended two fingers toward your forehead, but there was nowhere to go. As soon as he touched, with an evil smirk on his face, there was nothingness.

**~~**

You came to slowly, cracking your eyes open against the dull throbbing in your head, one of the first things you noticed was how cold you were. And naked. _Of course I'm still fucking naked._

The air was crisp and there was a breeze that made it clear you were outside. . but _where_ outside?

Through blurry vision you thought for sure Dean had dumped you in the middle of a forest, the top of a mountain, on a boat in the ocean - somewhere isolated and vague - but as you began to make out shapes through the dim light, you found yourself sitting in the middle of a neighborhood street in nothing but your birthday suit. _Oh real nice._

 _What fresh Hell is this?_ Not for one second did you believe you’d been set free. Not for one fucking second. For one, everything seemed oddly silent and surreal. . . The street lamp at the far end of the street was illuminating every house face dimly, which seemed odd to you, seeing as the light should have only covered about a 25 foot radius.

Another thing that made dread thicken your blood was not _only_ that the sky was pitch black, but impenetrable darkness occurred immediately after the lone streetlight like a curtain.

You couldn’t see any further.

Swallowing thickly and peeking over your shoulder you startled at the wall of blackness directly behind you as well, daring to reach out to it. . . Your fingers disappeared into the dark, feeling extremely cold as if you’d just submerged them in ice water,

“Shit!” you retracted quickly, listening to your exclamation echo around the eerily familiar neighborhood. The windows of every home were dark, staring at you with windows that resembled gaping dead eyes. You shuddered and did something that made you hate yourself,

“Dean. . .?” you fucking called for him. Like he wasn’t the cause of all of this terror in the first place. Honestly though this whole ‘nuclear test site’ vibe was giving you the creeps, and you just didn’t want to be alone in the deserted nighttime street anymore.

Suddenly a light flicked on in one of the looming homes on the first floor. A dim light but enough to catch your eye. _He’s there. . . He’s in that one. . ._ And then your brain gave a start as you really took a second to look at the house.

There was the dent in the garage door from when your father backed into it, a cracked window on the side of the house from when a branch slapped it in a windstorm, and a barbie doll dressed in pink sitting up on the mailbox. . . from when you put it there years ago before your parents split.

Your heart throbbed, beating through somber nostalgia.

This was your childhood home.

**Notes for the Chapter:**

> ??? Haha tell me what you think so far, I love to hear from ya'll :) 
> 
> The next chapter isn't going to be such a long wait I promise x1000000. Thanks for reading, hope you enjoyed the third chapter! One more to go loves <3
> 
>  
> 
> Come kink with me on Twitter @DirtyMind_Girl ;)


	4. Childhood, Ruined

**Summary for the Chapter:**

> Many feelings come to the surface upon recognizing your childhood home. The one that burned to the ground years ago. . . What kind of fucked up game is your demon captor playing?

**Notes for the Chapter:**

> If you're this far, you know what the warnings are. However I will say if you've lost a parent or both, and you haven't come to terms with it or adjusted, please be careful in this chapter. . it could really hurt you. And I enjoy triggering emotions, but not those kind. . I'm almost tempted to say don't read if that's the case. <3 
> 
> You can always come talk to me about it in the comments, before or after you read it. ;) Be safe!  
> Otherwise enjoy! :)
> 
> Also I tried a Dean POV portion, I needed to explain his feelings toward her. It's small so if you hate it, hang tight :)

All you could do was stare at the building in the eerie dim lighting.

You hadn’t seen it in years. . not since it burned to the ground the year you went to college. . It was like a punch in the gut seeing it now, looking the same as it did before the fire, before your childhood monument was ripped away, before your parents burned with it.

“Oh. .” it was sort of an outward gasp at the feelings banging around inside your head and heart. Only one thing made sense. There was only one way this house could be staring at you. You were still in Hell. Which, judging by the ominous blackness bordering the block, it made more sense than not. . _Night sky’s are never this dark._

You supposed that the light in the downstairs window was there to beckon you inside. . not that it was necessary really, there was no way you weren’t going in. It started as a fleeting thought at first, as you creakily rose to your feet on the pavement, but then it formed into a sad hope which developed into a devastating certainty. _My parents could be in there. . I’m going to see Mom and Dad again. Together. Like old times._

That idea alone made you move toward the ghost house, forgetting Dean for the time being in this need to see beloved old faces.

The chill in Hell’s air made you wrap your arms around your nude form, as your bare feet sunk into the grass that somehow injected nostalgia straight into your soles. _How can grass feel familiar?_ Climbing the steps was surreal, your wide eyes were drinking in every mourned detail, every little piece that you thought was lost forever - that was lost forever.

The screen cracked and offered to send you into a flashback right there on the splintered porch, but you gently denied for now. . there was a mission on your mind. _Should. . should I knock?_ You shook your head and reached for the knob.

Any fear that you should have had was eclipsed by the need to speak to your mom, by the craving to hug your dad, but your hand did tremble as it twisted the haunted knob, and you did stop breathing as you followed the door inward. It looked exactly as you remembered it, the living room to your right, the kitchen to your left, and the base of the stairs a few feet in front of you. .

Dean was nowhere to be seen, and neither were your parents, but if there was one thing you did well it was hang onto hope.

Taking a deep breath, you finally found your voice. Your very soft airy voice,

“M -Mom. .?” you stepped further inside, leaving the door gaping behind you. “Dad. . .?” it had been so long since you said their names that way, addressing them, calling for them. . Now it was all past tense and useless memories. It felt good, but also empty somehow.

Your heart swelled at the possibility that they might be there, that your mother would poke her happy little head out of the kitchen, or your father would rise from the couch, pipe in hand, to greet you with a wide smile. You missed that the most. Seeing their smiles.

However, the house was the kind of silent that made you want to freeze.

There was no way you were leaving, but at the same time you were scared to go forward. . so what you did was glance back at the door. You heart dropped at what you saw. _Blackness_. The same kind of dark that was just beyond those streetlights. . impenetrable, thick, ominous blackness. There was no going back outside after all.

Your shaky breathing was the only thing interrupting the quiet it seemed, and it only grew heavier as you moved slowly around the wooden banister into the living room. There was the light. The lamp that had been turned on to call you over in the first place. It was your favorite one when you were little, sitting next to your father’s sofa chair, all lit up with soft purple glass birds surrounded by opaque sky.

It looked so much smaller now. The only thing missing was your father, but it was like you could smell his sweet tobacco smoke as if he was puffing a pipe right in front of you,

“D-Daddy?” you swallowed, having been reverted to the little girl you were when you last spoke to him. No answer. “Dad?” and you moved further into the room, glancing at the dark hallway that wrapped around to the kitchen and led to the back porch. Again no one spoke to you.

“ _Hello_?” now you were becoming more bold, desperate to see your parents come to life like this corpse of a house magically had. So you treaded softly to the wrap around hallway, trying to ignore the panic tightening your throat at how gloomy the hall looked. You walked past the back porch without even looking through the glass window onto it, worried you would see some creepy skeleton family sitting out there on the deck in lawn chairs with permanent lying smiles. You shivered and kept your eyes forward on the entrance to the kitchen.

“Momma?” it echoed on the tile. The cheap fridge sat over near the blacked out window that would look on your yard if it wasn’t for the weird darkness outside. There was suddenly an image of the house floating in a dark dimensional abyss, with you trapped inside hanging in empty space. It made you dizzy.

However something drug you toward the fridge, perhaps the pictures spattered all over the front that had been lost in the fire. Old life beckoned. And one dead center, that you remembered from all those years ago, of your mother and father holding you caught your eye. That day was one of your many memories.

It was a picnic at the park a few blocks away, you were about 4 years old, and happy as can be sitting in the arms of both of your parents. So were they. Their smiles brought moisture to your eyes, and without thinking you snatched the picture from the freezer door and folded it in your hand. The magnet holding it went tumbling to the floor in a clatter, making the loudest noise that you had heard so far in the house, and for some reason you bent to pick it up. .

Like someone would come home and be upset to find it laying on the otherwise pristine floor. Just as your fingers snagged the little magnet, a loud thump sounded over your head - someone was upstairs. Magnet forgotten, you practically ran to the base of the stairs and grabbed the banister at the bottom,

“Hello?” you called a little frantically into the looming darkness of the staircase. Another thump. Holding the picture close to your chest you rounded the railing and flew up the first few steps, spurred on when yet another thump happened somewhere ahead of you.

“Momma?! Daddy?!” you cried sprinting up to the landing, even after all of these years your feet remembered where to go in the dark. You hit the landing and froze. It was silent, but clear that you weren’t alone. Still clutching the folded picture you reached out to your right and tried the hallway light switch, only to be given a click and no light. _Shit_. .

“H-hello?” you whispered tiptoeing on the hardwood to where you knew your childhood bedroom lie. Whatever was near you, it’s presence was malevolent and you thought about the reason you were here for the first time since walking through the door,

“ _Dean_. .?” the atmosphere answered even when he did not, it thickened in your ears and throat. He was there, watching. With your free hand, you felt along the cool wall until it indented into your bedroom door, you fumbled with the knob for a moment before it finally twisted and let you in. A light was on.

While still dim you had to blink against it as you basically went in the rest of the way blind, but as soon as your eyes adjusted you took in all that you had lost in the fire.

Plus a few extra things.

There was a set of handcuffs hanging from all four bed posts of your old bed. . the sheets were still pink like the used to be, which was a weird thing to notice when on your bedside table was a plethora of sex toys ranging from familiar to terrifying. And was that a. . . _flogger_? There was no air in the room and all you could do was stare. _Oh God. ._

When you finally got the clue that now was a good time to run, the door slammed loudly from behind, and you screamed as you spun around. Only then did you notice the warm tear tracks on your own cheeks. There he was, wearing his red button down and jeans, looking like the devil himself with a smirk evil enough to evacuate a village.

Instinctively you tried to cover yourself, one hand over your sex, and the other arm across your breasts. . which was silly since he’d seen everything anyway.

“D-Dean. .” it was a quiet breath really, and he didn’t even acknowledge it, nor did he attack you right away like you thought he would. He did move forward however, and you watched his boots leave imprints in the soft carpet. . for some reason you wanted to reprimand him for wearing those dirty things in the house. But of course you knew that was idiotic.

This place wasn’t even real.

“Heya sweetheart,” he rumbled quietly as he approached you. The demon moved slow, like he was afraid to startle you or something. . but even if you did bolt, you both knew he’d catch you.

“W-what _is_ this?” you took a step back, but edged away from the bed. Which was probably wise. Instead of answering, he only grinned mischievously, black eyes flickering to your fisted hand going across your chest.

“Whatcha got there?” he was asking about the picture. A thick swallow bobbed your throat, he was getting too close. Your eyes flitted around the room, “Not gonna answer me?” there was a hint of warning in his voice that snapped you back to attention. Your sore ass was too fresh to forget what kind of pain his anger could produce,

“It’s -it’s a picture. .” you whispered, taking another step back toward the window.

“A picture?” he was speaking to you like you were a child, his eyebrows were raised and everything, “Why don’t you let me see babygirl.” a tear dripped out,

“What _is_ this?” you asked again, and received a low sound of disapproval from the big man’s chest,

“The picture. I want to see it.” when his voice turned hard like that there was no stalling to be done, so you timidly extended your hand and hunched over a little to protect your chest from his black eyes. The tattered photo shook in your fingers like a dying leaf on a twig in the wind.

With a humored sort of snort, he took it, brushing his large rough fingers over the tips of your much smaller soft ones. The picture made a crinkling noise as he unfolded it,

“Ahh. . How cute. Betcha never thought you’d go from a giggling little girl in rain boots, to a naked wanton slut in the span of 20 years.” he sighed like he was having a carefree chat,

“I’m - I’m not -”

“So what, then? You wanted to take this as a keepsake? Missing it since it burned in the fire. .?” finally you looked up at him, and he had a teasing smile on his face - now green eyes glinting with ill-intent.

“Yes. .” and you reached for it, but not demanding. More of a plea, “Give it back.” he pursed his lips in a pitying fashion,

“Aw. . Does somebody miss Mommy and Daddy still? That’s so fucking cute.” your lower lip trembled, “Did miss the chance to say love you one last time?”

“Stop it.” you sniveled, feeling the tears winning the battle of pride. “Please.”

“Damn, the lady said _please_ , what the fuck am I gonna do now? Oh I know. .” and then he took the wrinkled picture with both hands and held it in front of your face, “This.” and he tore it in a swift jerk before throwing the two halves toward your face to flutter to the ground.

“No!” you cried, dropping to your knees to pick up the pieces, “Why would you do that. .?” now you were crying, clutching the remnants of the picture to your naked chest, and he squatted down to speak right into your face,

“Because I don’t give a shit about your pathetic little feelings, or what you want.” it was practically snarled, and his eyes flicked black with a wet sound. “Have I made myself clear?” you had to look away. You had to close your eyes and look down at your thighs, as if you were trying to cry in private. . but he was just on the other side of your thin eyelids, leering and watching. Waiting. Then with no preamble,

“Get on the bed.” it was low and husky, and it made your eyes come open.

“W-why?” he just looked at you with this darkened gaze like he was waiting for you to connect the dots. As if you hadn’t already. “No. . no. .” instead of getting angry, Dean just licked his lips and traced a big finger delicately over your toes, watching them curl away from the contact.

“Did you forget what happens to little girls who don’t listen?” no. No you didn’t. You shifted on your raw ass, “Does someone need reminding of how rough Daddy can be?” your face crumpled,

“ _No_. .” it was a tiny little whine, but Dean rumbled in acknowledgement.

“Good.” a beat passed, “Then get on the bed.” you looked over at it, staring at the handcuffs with obvious trepidation as you shakily rose to your feet. Dean stayed crouched, looking up at you, waiting to see what you’d do. “Last chance sweetheart. .” he warned from down below, “Either do it yourself or I’ll help you.”

“Are. . are you gonna hurt me?” you whispered, still glued to the floor. His face darkened, and he rose up from the floor to tower over you once again. You stumbled back a fraction,

“If you don’t get in the fucking bed I will.” a single sob busted from your chest, but you managed to edge along the wall to the edge of the mattress and sit. He remained standing where you left him, calculating and observing. Always an inch away from exploding. The demon might have looked normal if it wasn’t for the growing bulge in his jeans as he looked at you, the sight made you whimper and shake.

 _He’s gonna rape me. ._ He smirked with a short airy laugh,

“Like what ya see bitch?” more tears flooded out, and your heart hammered when he finally moved toward you. There was a sad attempt to avert your eyes from his ever-growing member on your part, but you squeezed your thighs tightly closed and kept both arms over your breasts. “Lie back.” his deep voice made you jump,

“N - no. .”

“Lie. Back.” it was said through teeth, and he watched you look around the room for any kind of help. But you knew as well as he did, you were out of options.

“Dean -”

“Lie back, arms over your head. Don’t make me ask again, or it won’t be my hand I use to turn your sexy little ass red.” you gulped and glanced at the nearby flogger on accident. When you looked back up at him, you were surprised to see he wasn’t exactly angry yet. . he almost looked _curious_ , “Tell you what, you do this without a fight, and I’ll actually let you get some sleep tonight. Plus I won’t beat the shit outta ya. Sound good?”

No none of it sounded good, but whatever involved the least amount of pain and humiliation was the road that you were going to take. Both you and Dean knew, that he was only playing with his food. He could hold you down and fuck you in half at any given moment, but he wanted to play, to scare, to _break_. That’s the only reason he was even speaking right now.

So reluctantly and stiffly, you laid back and settled for closing your eyes when you lifted them from your chest and over your head, both legs were still cemented shut. You felt him bend and stretch each arm to it’s corresponding bedpost to cuff your wrists.

Only the jingle of his belt buckle made you snap back, and his upper body was totally void of clothing already. You inhaled sharply at all that bare skin, heating up despite yourself. . like some part of you recognized how sexy Dean was, while the bigger portion of you was just afraid of him. _How can someone be more intimidating with clothes off?_

“What are you doing?” he was removing his belt from the loops, and for a terrifying moment, you thought he was going to whip you with it, but he cast it aside and went for the button on his jeans. You tried to bring your arms down, but they caught on the cuffs.

If there was one thing you would learn from this it’s that it is always possible to be more terrified than you already are.

“Wait Dean, you - you said you weren’t gonna hurt me.” he flashed his white teeth in a wolfish grin as he pulled the zipper,

“No. What I said was I would hurt you if you didn’t get on the bed. . I never said I wouldn’t.” your whole body went cold at his words.

“P -please don’t -” a gasp cut off your tremulous voice when his jeans dropped slightly lower on his hips, springing his erection free. He was the biggest you’d ever seen up close and personal, and what may be a pleasant surprise for other conquests, it was a horror for you.

They were willing. You _weren’t_. “Oh. .” you breathed watching it, like it was gonna detach and rocket into you from three feet away.

It was strange seeing that part of the demon, it was as if his confident aura flowed right into his manhood - it was up and at attention, thick and long, almost leering at you in a way that made you fear it.

Just like it’s owner. Just like your owner. Dean stepped forward, never dropping his jeans all the way, and gripped his erection almost violently, making your eyes widen as they lingered,

“You make me hard .” that was the first time he ever used your name, and it made your chest tighten in the strangest way. “Seeing you like this, naked and bound, makes me so fuckin’ hard.” your body tightened up more at his ominous words, and then he said the most frightening thing he could have right then. “Let me have a look at you baby.”

Almost instantly you tried to curl up away from him, but found it difficult without your hands, and when his big rough hand wrapped around your ankle you actually screamed. So he jerked your whole body back into position, flat on your back, and clamped a hand hard over your mouth,

“Be still and quiet. I just want to look at you, understand?” you shook your head, struggling, and he pressed down harder. You tasted blood, but didn’t linger on it when his hand shifted slightly and sealed against you nostrils. _No air. No air!_

Dean took a knee over your thighs and leaned on you, quelling your frantic flailing and looking into your eyes with cold merciless green ones. _Is he going to kill me?_

“Still and quiet. You got me?” tears were soaking the mattress below when he finally released you sit at your feet. You worked to follow his orders, fearing more than anything the demons anger. “Good girl.” he practically purred while he studied you.

It was unclear why this was so hard to deal with. The guy had his face in your pussy only hours ago for crying out loud! But there was something different about this. . he was studying you - not like he was looking for flaws though - like he was appreciated every inch of your layed out body. It gave you goosebumps. His sharp green eyes lingered on your pussy as they roamed your body and you waited with every cell tensed for what he might do. . but the way he was looking at you was causing a certain emotion to nudge fear out of the way a little. . Only a little.

Your cheeks flushed. However Dean broke the spell with his next command,

“Pull up your knees and spread them. Feet flat on the bed.” your toes curled at the same time more tears leaked out of your eyes. . it was _confusing_.

“Please, Dean.” you whispered, sniveling and quaking under his heavy gaze.

“I’m sorry, what did you call me?” _oh back to this_. . you took in a choppy lungful of air.

“P- _please_ sir. .” a corner of his pretty lips lifted, but he still only waited for you to do as he said. With a scared sob, you brought your knees up but couldn’t bring yourself to open your legs. He growled, “I - I can’t. . I can’t I’m sorry. .” you wept, unable to see his face now because of your knees.

“You will.” dark. His voice was so dark that your knees very slowly began to part, knocking together at first until they were too far apart to touch. Like a curtain, the movement revealed the demon's face again and he was zeroed in on your sex.

As soon as your thighs were spread wide, his eyes flooded black - when you whimpered he looked at you, and continued looking when he moved to brush his calloused fingers on the spot where your butt met your inner thigh. With a gasp you slammed your leg closed,

“You said you just wanted to look!” how foolish that sounded. Of course he wasn’t just going to look. . he wanted to fuck you, if that solid rod coming up out of his open jeans told you anything.

“Shh.” he hissed, with the fingers still between your legs, “Open.” one thick digit wiggled over to your slit and brushed over your clit. You jumped and gasped, “Open your legs. _Now_.” the finger that was brushing over your nerve bundle eased your decision a little, and you parted again for him, jumping when he spread open your lips with two fingers.

“You have such a pretty pussy.” he rumbled somehow conveying lust through those onyx eyes, “I can smell you . I can smell how horny you are. Need somethin’ sweetheart?” you gulped, nostrils flaring while he held your pussy open to the cool air of the room. You did need something. . bad. But there was no way you were asking for it.

“Hmm, let me just -” and before you could process the big man leaned down and ran his hot tongue up along your slit, and you jumped, spreading your legs wider instead of snapping them closed. He sat straight again, “Mmm, yeah definitely horny.” he commented with a half smile, “I can taste it too - it tastes like woman. . better than pie. What would you say if I wanted to eat your pussy for every meal hmm?” your face burned.

 _Why is he doing this? Why not just fuck me and get it over with?_ He licked his lips and a tiny moan escaped yours at the sight. . _Oh dear Lord_. .

“Yeah thought so,” and then he leaned back down, somehow spreading you even wider for his mouth before blowing on your clit. You bucked and he gave it to you with a sudden slide of that velvet spear from your swollen hole to your clit and back again, it made you lay your head back and turn to jelly. The demon nibbled and kissed the sensitive lips, allowing you to squirm around under his tongue for a while and heat up - your whole body was flushed when he brought those full sinful lips to your throbbing clit and kissed it once, twice, _three_ times, with maddening pressure,

“Please. .” you mewled, thrusting your hips upward like an offering. In response he brought his hand down hard and slapped your pussy hard enough to make you scream and jerk. There was no denying an electric shock shot straight to your clit at the blow. _Fuck_!

“Use your words,” he chuckled, as you fell back to the mattress, only to have him strike you again. The wet slapping sound was humiliating, but the sting was too real, the arousal too disconcerting.

“Ow! Ahh, D-Dean _stop_. .” you jumped when he pressed a kiss to your clit again, “Please!”

“Please what?” he laughed, lapping a couple hard licks at your sensitive mound and chucking when you jumped each time, “Want me to suck on your little clit? Would you like that baby girl?” you sobbed at his words, almost coming just by the sound of his deep sexy voice.

“Y-yes.” you admitted, tensing when you felt his lips seal around the nub. He sucked. _Hard_. “O- _oh_! Oooooh. . .”

“Like that baby?” he did it again but left his mouth there and totally went to town sucking and licking at you, building up the fire until you were about to burn to a crisp. His stubble was rubbing you raw at the thighs, but compared to his pussy lavishing you could hardly feel it - or care. Upon looking down on him for the first time since he started, you found that he was watching you with solid black eyes, but the visual of his swollen pulsing lips squeezing and suckling on your clit made it okay. .

His tongue was swirling at you, bringing you to the edge quicker than that vibrator ever had. . there was something about having a man down there that did that to a girl.

“Oooo oh God Dean - I’m g-gonna -” the only warning you got was a smirk and a wink before he pulled off of you completely, “ _No_! W-why, why?’ you jerked on the cuffs, desperately wanting to finish yourself off.

“You wanna come? Go ahead,” and he sent his hand vaulting to your sex again, harder than he ever had, but the contact on your needy pussy did something other than bring tears to your eyes. It hurled you into orgasm.

“Oh f- _FUCK_!” you were trying to grind against nothing while Dean rose up from the bed laughing like an asshole, as your climax sputtered and died like a fading light. When you caught your breath you noticed that he was beside the bedside table, looking down at his array of toys, vibrators, clamps, and blindfolds. Your throat caught when he chose the riding crop, and again when he slapped it down on the wooden table.

_Oh. Shit._

“Be really still for Daddy and I’ll give you a reward.” he leered while running the crop over your trembling flesh. There were tears coming out of your eyes, but it wasn’t really due to fear anymore as much as confusion. _What’s happening to me? Why can’t I stop coming with this demon?_

People got spanked with these things all of the time, and you figured that so long as he wanted to play Master/Slave you could get through it. It was when he started burning you to the bone with acid, and cutting off your nipples that would really put a damper on your time in Hell. So oddly enough, knowing that he was about to lay into you with a riding crop made you feel lucky.

Still, you jumped when the demon began to run the leather along your skin, and he gave a low dark chuckle - both of those things gave you goosebumps, and made your nipples go up into stiff peaks,

“Such a sexy little slut. .” he mused, “Where should I hit you first, hmm?” the crop caressed your upper thigh, “Spread your legs bitch.” with a quaking inward breath, you did. “Being such a good little girl for me. . . Tell me where to spank you.” your eyes flew open. _Is he serious?_

“Nowhere.” he actually busted a laugh,

“Cute. Now pick a place before I start wailing on your pretty pink pussy.” that made you shiver,

“Um m-my,” _what would be the least painful?_ “My foot.” your face reddened at how weird that sounded, but Dean nodded with pursed lips and delivered a sharp blow to the bottom of your foot. _Oh fuck that hurt. ._ Even on your foot it made your eyes well with pain.

“Next.”

“Thigh.” _THWACK_! “AHH!” _that stung like a son of a bitch_ ,

“Ooo that one hurt ya a little more?” he was laughing, “Next.”

“M -my hip. .” you sobbed. _SMACK_! “A-ah. . _ow_. .” you wept. Dean was really hitting you hard.

“Well?”

“Please stop.” you begged softly, once again seeing his sharp canines in a wide smile,

“Next baby.” you eyes shut tightly,

“My stomach. Please not hard -” _CRACK_! “DEAN! Fuck, fuck, _fuck_. .” and then before you could even request another place, he began raining blows all along your front, at first he skipped the sensitive spots. . . At first. The second the leather connected with a nipple your body jumped off of the bed,

“No!” you were screaming and crying loud enough to wake the neighborhood - if there was one. Your other nipple took a blow, and then he shifted direction and brought the crop down right on your pussy.

The pain was so intense that no noise came out of your gaping mouth, and your bugging eyes saw nothing but white. Before you could even recover enough to breath Dean cracked it down on both of your nipples and was trailing it back to your stinging sex.  _No! Nooooo!_ The words wouldn’t come out, not that it would have mattered,

“It’s a little ironic how you begged me to let you come, and it only made you more sensitive for this. Humor in the little things I guess. .” he mulled to himself, before he lifted the crop to deliver another devastating blow to your sex. That time you did scream, and then again when his fingers were on your slit, and again when those fingers started rubbing.

“N-no. .” you jerked and writhed against the pain, crying out endlessly when the demon began striking you with the crop randomly on your body while his fingers picked up the pace.

“If you come, I’ll stop. . but honestly? I could watch you scream and cry all night long.” your hips spasmed when your sex pulsed despite the never ending blows from the crop.

“Stop!” you wailed, “ _Stop_ it!” it fell on deaf ears, for the torture continued. There was no way you were gonna come like this. . the pulsing of your clit disagreed, and as if Dean felt it throbbing under his fingers, he increased the pressure on your abused nub.

And then - against your will - you were coming again. It was a miracle. This climax almost painful in it’s intensity, as you jerked and bucked around on the bed, popping your shoulder with an involuntary spastic movement. When you had ridden it all the way through, Dean moved off of you with a knowing smile - _he just forced me to orgasm. . How in the Hell. . ._

You laid there dazed, not even registering that he released one of your hands from the bedpost until he tossed your jellied arm to your side. .

“Dean. .” you groaned, for no reason really other than to say something,

“Yeah baby,” his head tilted your direction from his table of toys,

“I. . I’m. . . _fuck_. .” when your sentence just kind of faded away, the man laughed this genuine laugh that you’d never heard before from him. You imagined that’s what he would’ve sounded like when he was human.

But for some reason you started to cry quietly. . at the whole situation you assumed, from how much your skin was stinging, to the fact that you were in your childhood room, and knowing that instead of good memories when you thought back to it. . you’d think of this.

Of being chained to a bed and sexually ravaged by a demon, instead of sitting on the floor eating raw dough from your easy bake oven. His deep voice rumbled into your thoughts,

“Alright doll, what’s next. . Any requests?” you only wept quietly, still stinging from the beating and still shaking from the forced orgasm. “Ahh, I know. How about a little treat for you? You’ll like this. .” it was weird because he sounded genuine, like you really would be happy with the next choice. The sound of an opening drawer drew your attention, and when you got a load of what he pulled out, you found the strength to shimmy up the mattress.

The fear was back. And your next two words were really just sobs.

“N-no! No-o-o-o!” you wrapped an arm around both knees, and shook your head at the mildly surprised looking demon. In his hand was a big pink dildo. He was gonna fuck you with it. With curiously narrowed eyes and a small interested smile on his face, he stepped back toward you, no doubt seeing that your eyes were trained on the big plastic toy,

“Dean - Dean no. No - no - no. .” you were close to sobbing again, but there were torrents of warm salty tears cascading down your face.

“Well shit, I woulda thought you’d be excited about this.” he cocked his head like a thought just occurred to him, “You’re not one of those girls, that has a dildo phobia are you?” the way he was looking at you made it clear that the idea pleased him. Sick bastard.

Honestly you didn’t _think_ you had a phobia, then again you’d never used one, and the way that fake dick was making your chest tighten was troubling. Your explanation was a shot in the dark, and your voice was high with tears,

“No, I’m one of those girls that’s afraid of a Knight of _Hell_ shoving something that big inside of her.” close enough you supposed, Dean’s teeth gleamed in the dim light when he grinned,

“Baby, this ain’t that big.” glancing at his throbbing dick was unavoidable, and yeah he was significantly bigger, which didn’t make you feel better at all.

“Stay the fuck away from me with that thing,” his eyes snapped black at your tone, and it all went to Hell. So fast you hardly had time to scream, Dean snaked his arm beneath your knees and forced them up against your chest, barring them down with his weight and muscled forearm. You grunted and tried to push him off but he was much to heavy, and he had effectively exposed your ass and pussy for the viewing of his sharp green eyes.

“Get off of me!” you gasped, finding it hard to breath with the pressure he was putting on your chest. You squeaked at the feeling of that horrid rubber toy rubbing into the skin of your thigh, and redoubled your efforts to get out of that position. In vain of course, Dean was actually laughing at your panic now.

“Don’t - don’t touch me with that thing!” you cried desperately as he brushed it down toward your vulnerable sex, “P - _please_!”

“Aw, so polite all of a sudden huh?” his casual attitude made you sob, “What’s the matter baby? Afraid of this little toy?” _Little_? No it wasn’t little by any means, and there wasn’t a doubt in your mind that Dean would purposely hurt you with it. . . That’s why you were there in the first place right? To be tortured?

“ _Yes_. . .” you sobbed, hating the way it made him grin, “Please don’t use it on me. . . I - I don’t -”

“Oh come on, take Daddy’s toy like a good girl.” he smacked it down on your pussy and you bit back a cry at the sting, “I bet you open up nice and wet for this, huh?” he rubbed it firmly along your slit,

“No. . . no _please_ , I don’t want it. . .” your begging was practically unintelligible at this point, just strings of high pitched slurs really, “ I - I did everything you asked, please, I’ve been good. . don’t hurt me with that! Please, _please_ Dean. .” you were hiccuping and choking on sobs, straining with the cuffs and tensing for a sudden entrance from the toy.

Sharp teeth became prominent on your thigh right next to your core, where he was still sliding the dildo around leisurely as if you weren’t a sobbing mess beneath him. He was nibbling and kissing the backs of your thighs gently like he was a lover instead of a monster,

“What makes you so sure I’m gonna hurt you?” he pondered lazily, “Have I not made you come sweetheart?” you were bawling so loudly it was a wonder you could hear him, when you didn’t answer he pushed on your entrance firmly and you locked up everywhere, “What did I say about answering me?”

“S-sorry!” you cried,

“Have I made you come?” he repeated darkly,

“Y -yes sir,” your voice was strained with the discomfort he was causing on your opening, but as soon as you spoke he let up a little,

“So take this dick like a good little girl, before you piss me off. Or I might decide to use my own.” the warning only scared you more,

“No, no, _no_. . . please don’t make me!” you pleaded with the demon, knowing it was useless.

“Why are you so afraid of a toy baby girl?” that brought you up short. You were unsure whether you should tell him the truth, but when he began applying pressure again it just came out,

“Y-you’re trying to _hurt_ me,” the man only chuckled, baring down on your aching sex just enough to make you scream. It was too much and it had been way too long since you had last been with someone. . you might as well had been a _virgin_.

“Shut the fuck up.” he growled pushing on the toy once again, but the action only spurred on your babbling and suddenly the very tip of the thick toy was breaching your opening,

“Ahh! _Ow_ \- no, no _stop_!” you begged, locking up all over at the intrusion. At your words, Dean paused with only the first inch of the toy inside of you.

“You stupid little cunt,” he snarled. You were trembling so violently that the handcuffs were rattling on the headboard, “screamin’ and cryin’ like I’ll give a shit. . .” his hair tickled the bottom of your raised foot while he shook his head, “I don’t give a shit, why would I?” but he stayed frozen, just barely inside of you.

“ _Please_ Dean. . . It h - _hurts_. . .” you sniveled, just praying he wouldn’t push in. And with a loud terrifying roar, your prayers were answered. Dean pulled the dildo out and shoved off of you, letting your legs drop back on the bed as he sat back on his heels,

“Son of a bitch!” he thundered with such rage you swore it shook the house. His black eyes tracked you, scooting up to the headboard to cower away from him and that blasted rubber dick like it was going to come to life and fuck you itself. You flinched when he threw the thing into the far wall with a vibrating thump and another aggravated growl.

 _Why was he doing this?_ Why would a demon not rape you. . .? Especially after you it was obviously hurting you? That seems right up an evil entity’s alley. Dean pinned you with barely controlled black eyed rage, that had you so petrified you began apologizing to him for some reason,

“I’m sorry, I’m _sorry_ \- please - I’m sorry. . .” you curled up tighter and hugged your knees close as he crawled up the bed toward you, with a look in his eye that screamed murder,

“You think you’ve gotten out of this?” he growled, and you just stared, “Not even close. Oh, I’m gonna fuck you alright sweetheart, and it’s gonna be on my terms. You just wait for it.” fat dumpy tears rolled down your cheeks at his harsh words,

“ _Nooo_ \- o - o,” you wept quietly, pleading with your eyes, “P - _please_ no. . .” he raked his eyes over you looking almost disgusted before shaking his head and heaving off of the bed. It wasn’t necessarily that fucking him sounded so horrible, after all he wasn’t a bad looking guy by any means, hottest guy out of the two you’d been with by far. . but what made it unbearable was the fact that he wanted to hurt you - he wanted to cause pain.

And for fuck’s sake he was a _demon_! He didn’t care for you - couldn’t - there was no love in him. You watched the monster in question, shaking like a leaf, and he cast one last glance at you before his hand snapped the lightswitch down. The darkness made the sobs come louder, feeling impossibly more vulnerable now that you were essentially blind.

“Shut the fuck up,” the bed dipped, and you tensed all over waiting to feel a big rough hand somewhere on your skin, but after not breathing for a solid two minutes, it never came. You still didn’t want to move, as if it would remind him you were there and strung up for the taking. Another few silent minutes passed, filled only by your shallow breathing and the occasional quiet snivel, you jumped at his sudden rough voice,

“I can’t sleep with you shakin’ the whole bed,” he griped in surprisingly mild irritation, “would you calm down already?”

“S -sorry,” you whispered tremulously, unable to still the tremors still coursing through you,

“Just lay down, seriously.” while the words were sort of kind, Dean sounded grumpy, and although you were sure that he was going to jump you as soon as your head hit the pillow, there wasn’t a bone brave enough in your body to defy him. So you gently, and nervously inched down the bed until you were facing away from him on your side with both knees curled up to your chest and one arm still cuffed to the headboard.

Another involuntary snivel jerked you body. You just couldn’t make the tears stop,

“ _Shh_!” the man beside you hissed harshly, and it only built your smothering fear. While the room was silent it felt like your mind was buzzing loud enough for him to hear, and it wouldn’t stop crowding devastating facts and concerning questions into your head.

_I’m in Hell with a demon, a knight of Hell he said. . . He’s already promised torture. Not good. That dildo scare probably just added to his list of torment. . . that’s why he didn’t rape me yet. He’s probably just concocting the perfect sadistic plan in his head to make it as horrific as possible. Oh God he’s gonna hurt me so bad. . ._

A sob burst out in the quiet room, and you froze but Dean remained silent. It was probably music to his ears. _How am I gonna get out of this? Can I even escape Hell? Am I . . . Dead? How did he know this was my childhood home? He fucking carved his initials into my back. I’ve climaxed three times with - a demon for God’s sake._

And you found it odd that he hadn’t asked for anything in return. You wondered when that anvil would drop on your head. So caught up in your thoughts, you didn’t realize that your crying - while still quiet - was completely audible, you hadn’t stopped shaking, and you were too distracted to notice the displeasure rolling from Dean in waves. Until finally he voiced it,

“Ugh fuck, do you ever shut up?” you froze and stopped breathing, the anger in his deep voice was chilling. When you knew for sure that your words would come out intelligible you let them out,

“I -I’m sorry,” more snivelling and hiccuping, followed by a loud heavy sigh from the demon beside you. His obvious irritation triggered the beginnings of a sobbing fit, still quiet, but audible and painful to hold in your lungs. When you heard the bed creak you whimpered, and glanced back over your shoulder to see Dean sitting up on the edge of the bed bent over slightly to rummage through the nightstand.

You turned forward again and squeezed your eyes closed with a low sob, cringing when the bed dipped right behind your back.

“You want me to give you a reason to fucking cry?” you curled up tighter and shied away from him, “Is that what you want sweetheart?” his big warm hand skimmed your back, and you cried out loudly, struggling to scoot away from him with one hand still attached to the headboard,

“ _No_! No - no - no. . .” you sobbed, coming very close to falling off the edge of the bed, but he just kept following you. Dean’s hot breath came up on the back of your neck, so close you could almost feel his lips there coaxing your little hairs to stand tall.

“Then shut. _Up_.” he growled in a soft voice. Sucking in a huge choppy lung full of air, you tried to do as he said, you really really did. . . but it was a lost cause. Horrid frightened noises continued to escape past your pursed lips, and your entire body was vibrating with tremors no matter how small you managed to curl up on your side. Again his hand made contact, this time brushing over your naked thigh lightly, coaxing high pitched shrill weeping from you.

He was terrifying. . . and he knew it. All calculated, cunning, intelligence. And every bit of it was focused on you and how to scare you within an inch of your life.

“See I think I need to give you a reason to cry baby,” he ground out huskily, skimming his thick fingers over the crease where your thighs were clamped together, “I think you’re forgetting all that I’ve done for you.”

“No -no,” your voice was so strained it sounded almost like a croak, “please don’t do anything to me. . . _please_ I’m sorry, I swear I’ll stop.” you hiccuped again on tears, fighting not to grab his exploring hand,

“No. . . I don’t think you will.” he mused, walking his fingers up your bare hip lazily, “But that’s alright, I can fix that.” he shifted on the mattress a little and you tensed, expecting the worst from him, but when some sort of fabric pressed against your lips you panicked. With a muffled cry you twisted your head to the side, only to feel the mystery strip stay on your mouth,

“Fighting me isn’t a good idea sweetheart, you want me to be rough?” he already knew the answer to that so you didn’t bother saying anything, instead you just focused on keeping your mouth closed against the material. However Dean nuzzled his face right into the crook of your neck and bit down on the folded flesh there, making you scream and jerk in pain, and as soon as your mouth opened the strip of fabric moved in.

It tightened around your cheeks and pulled uncomfortably at the corners of your lips. A _gag_. Dean gagged you.

“There we go.” after he had knotted it behind your head, he planted an out of place kiss to your ear and flopped back on his side. “Now stay quiet and try not to piss me off.” easier said than done apparently.

**Dean P.O.V.**

_Okay so the gag might have been a dick move. She still wouldn’t shut up. ._ If anything it had scared her more. That’s what he wanted right? _Bitch thinks she can manipulate me with all that crying and begging, but she’s just like the rest of them. . ._

At least that’s what he kept telling himself.

If he was being totally honest there was something inside him that longed to. . . _protect_ her? _A knight of Hell having feelings for some random slut. Yeah that’s ridiculous, I’m just a little off my game._ But there’s another part of Dean that knows deep down, had it been any other girl, he would have shoved that dildo straight through her cervix just to drink in the screams.

So what’s so different about this one?

He didn’t know, and that pissed him off. It caused clashing urges, some to torture and cause pain to the one who confused him, and some to comfort and sooth her. That’s not what he was doing right now though, as she continued to keep him up with her incessant crying.

Just before he was about to yell at her for it, a little voice reminded him that she was only frightened and that it was his fault. Which made him more angry. _I don’t give a shit!_ He wanted to scream that into the room, but it would ruin his calm menacing front, that seemed to terrify her more than anything.

That’s why it was so confusing to him. He wanted her fear, needed her tears, but also wanted. . . _her_. And right now it was pretty clear that she did not want him. The bitch was probably used to vanilla sex and cuddles.

The demon in him didn’t know whether to laugh or vomit, but the human - the _real_ Dean Winchester that was smothered inside somewhere - felt pity and compassion. God it made him want to roar. _Wasn’t the point of being demonized, not to care about being evil? To have fun doing it?_

Dean’s Hunter soul was too strong, had he been a normal man to begin with there wouldn’t be a problem right now. Hell, he’d probably still be fucking the shit out of her with that rubber dick. Another sob from the girl in question grated his nerves, and he actually felt a growl rumble through his chest, relishing the way the primal sound made her tense and whimper.

God that fear was potent and addicting. . . He wanted to feel it against his skin, and as he rose from the bed that’s exactly what he planned on doing.

As a demon, Dean could see clearly in the dark, but even if he hadn’t been able to it would be obvious that the girl was panicking already. She was whimpering and curling up like any amount of that would actually save her from whatever he was planning.

He wondered, as he rounded the bed, why women never really fought - not like men whose first instinct would be to fight him - they basically always resorted to crying, running, or even trying to make themselves a smaller target. Which is what this girl was doing right now.

Not once had a human woman ever fought with Dean, not even when _he_ was human. Thinking back on it there were perfect opportunities to get a hit or two in on him - during necessary break ins, misunderstandings, and overwhelming come ons - but more often than not they would just go limp and cry, like they knew it wouldn’t matter anyway. Like they were afraid to make him angry or something. . . _how tragic._

 _Waste of a potentially good wrestling match right there._ And by good of course he meant sexy.

“Even with a gag you still can’t be quiet. . . what am I gonna do with you?” he had rounded the bed to her side, standing just in front of her close enough to touch. He drank in her naked body leisurely, knowing that anticipation in these types of situations was really the scariest thing he could do.

Dean sighed dramatically, relishing the way she shook and mewled like a nervous Chihuahua under his gaze. So receptive, so fragile. . . He took a seat right below her toes which was basically on the middle of the bed because of how curled up she was. Her breath hitched at the sudden proximity change but other than that she was relatively quiet.

Unsatisfied, Dean reached out and laid his palm across the soft swell of her ass. She jerked away and he followed, until she started babbling through the fabric again. _Perfect_. Kneading and pinching her skin, Dean allowed a smile to grace his words,

“What’s the matter baby?” more unintelligible strings of begging no doubt, “I can’t hear you sweetheart, you want me to touch you more?” he moved his hand lower down her curve until his fingers were brushing over her bare sex. It was like she didn’t know what to do with herself. She didn’t want to straighten her legs because she’d touch him, and she couldn’t block her pussy by curling up tighter, so she just started sporadically flinching around until he took his tickling fingers away.

“You want me to take the gag off so you can speak baby girl?” ever so slightly she nodded like she was worried it was a trick. “Alright then you gotta do something for me.” she whined nervously, sending an odd pang of guilt into his chest, but he masked it with a low chuckle,

“All you have to do is roll flat onto your back for me,” her eyes squeezed shut again, and what could only be the word “ _please_ ” was muffled over and over again by the gag. _She thinks I'm going to rape her._ Normally he’d have let her believe that, but for some reason he said,

“I won’t touch you, no tricks. Just roll over and I’ll take the gag out.” Dean stood from the bed to give her room, and after a moment of mental debate from his victim, she finally turned stiffly to her back and flattened her legs onto the mattress.

“Good girl. . . That wasn’t so bad was it?” she was now splayed out, every inch of her skin completely visible to him. However she probably didn’t realize how well he could see in the dark. Dean did as promised and removed the gag, it was soaked in drool and tears, so he slapped it down on her right nipple without warning. It made a sharp snapping noise followed by a pained scream.

That’s how it should be, she was getting too comfortable,

“That’s what you get for keeping me up bitch,” he snarled, “you have any idea what I want to do to you, huh? Do you? There isn’t a thing you could do to stop me if I decided to take you right now baby.” she went totally still, staring at him with this gaze that was well beyond fear, it was unlike anything he’d ever seen. . and fuck it made his dick twitch.

Dean couldn’t remember the last time he’d scared someone so badly, and the girl was giving the Mark everything it need. . everything except blood that is.

**Your P.O.V.**

Despite the big man’s devastating threat, he sighed heavily and rounded the bed back to his side, flopping down and scooting near you. You didn't’ dare move, or breathe, or speak.

“Goddammit. .” it was growled to himself just before he gripped the hand cuffs and _ripped_ the chain clean in half with a hard jerk. _Holy shit._ . Now both of your hands were free, you just had an odd bracelet.

“What are you gonna do now?” you whispered, jumping when he wrapped an arm around your hips. The demon drug you close, turning you so that your front was facing his, “Dea -”

“Shut up.” he said it softly, but instead of doing anything scary. . the black eyed monster just held you quietly. _What the fuck is going on?_ Your body - tense and ready for another assault - began to relax into his warmth as you inhaled his spicy masculine musk, letting yourself believe for a moment that he was just a normal man. He pressed himself into you, while squeezing firmly with both arms, and you felt his erection against your thigh. . it made you stiffen,

“Are you gonna f- _fuck_ me?” you stuttered, earning a soft sigh from the large man,

“No, go to sleep already.” honestly you didn’t know what made you do it, maybe the desire to stay in his good graces for longer or something, but before you could register what was happening, Dean’s thick cock was in your hand. He went rigid.

“What -” but his question was cut off by his groan when you squeezed his thickness, your hand didn’t even wrap all the way around it. Then you were pumping, firmly squeezing his length up and down, up and down, with a practice that had him bucking into your hand.

These airy little breaths were puffing out of his mouth just above your head as you worked, and upon looking up to him you found that his eyes were closed and his lips were parted. _How could he manage to look prettier?_

Suddenly there were large fingers wiggling between your thighs, but it didn’t scare you as much as just make you worry a little. . Dean took no care as usual, and gripped your thigh to throw it over his hip, spreading you wide for his hand. You pumped him faster, hoping that it was enough to keep him out of your pussy for now. His fingers however met your glistening folds once again, and he gently pushed two thick digits inside,

“Oh . . _Dean_. .” you breathed, clenching on his hand,

“Yeah, baby let go like this.” he scissored his fingers while you twisted your hand around his shaft, pressing your thumb on the slit of his dick until he grunted with pleasure. Those big fingers massaged your walls the way a lover might, and it had you sighing and rocking into him, fucking down on his hand like a dog in heat.

Then, without much thought, you tilted your face up to his chin and kissed along his jaw, relishing the way his coarse hairs were rough on your lips. Dean’s dick jerked in your hand a couple times, signaling his upcoming release, and he began to thrust his fingers into you at a pace that had you constantly moaning.

He paused for a second to begin working a third finger into your tight canal, and you tensed up when it started to breach your hole,

“ _Ahh_. .” you mewled, “Dean too much, I th-think it’s too much.” but he didn’t relent,

“No. Relax and let me in. .” he breathed, bringing his lips down to yours to capture your whimpers in his mouth, and cupped the back of your head with his free hand. You consciously worked to go slack as he gently but firmly worked a third finger inside of you,

“ _Oh_. .” it was muffled on his mouth, and at the word he pushed his tongue past your lips, now massaging both of your openings expertly. He humped into your hand to get you going again, and you immediately did, not even realizing that you stopped in the first place.

Dean’s hot tongue fucked into your mouth, groaning and breathing as you worked over his cock, speeding up when his fingers did. Your toes were curling over Dean’s hip and you were squeezing his fingers so tightly that he was having to use those fabulous muscles to shove them in. It felt so fucking good. . and so did the kiss. It was the first time he really kissed you since he captured you. . like this anyway.

Again Dean’s dick pulsed in your palm and with a sexy grunting moan he spilled all over your inner thigh, just under where his fingers curled and slammed into your g-spot, brushing his thumb sideways over your clit with each thrust.

“Ah!” you cried into his mouth, biting his plump lower lip a little bit when he practically bruised that glorious spot with quick insistent thrusts.

The thrusts were so fast, it was almost like he was just jerking his fingers up and down inside, battering your g-spot until you came so hard you felt yourself gush around his fingers and then he pushed as deep as those long rough fingers would go, wiggling them around as wave after wave of pleasure made you jerk and scream against him.

When you finally came down, Dean was nibbling at your earlobe and then planting soft sweet kisses across your cheek to your lips, and when he got there it was the hottest kiss of the night and it lasted for a long time.

“Damn baby, I gotta say you ain’t as innocent as you led me to believe.” you didn’t even bother saying anything, flinching a little when Dean pulled his fingers and blushing hard when he sucked them clean. At the taste of you, his eyes flooded black and despite what the two of you had just shared, it made you nervous. He smirked,

“Scared of my eyes little girl?” he chided, as he settled and allowed you to turn over and away from him,

“No. .” you started, “I’m scared of _you_.” he huffed a short laugh behind you, pulling you tight,

“Good answer.” Somehow you fell asleep like that, with a demon warming your back, and his seed staining in between your thighs.

******

You woke up shivering to a pitch black room. No one was keeping you warm anymore. . Dean had abandoned you in bed. _For good? Probably not._ . but something inside made you slide from under the covers and make you way to the bedroom door.

Your body was sore, your pussy was sore, and honestly your _heart_ was sore. . Being in this house was soul crushing, and being with this demon - allowing yourself to jerk him off willingly? - that was devastating.

_I need to get out of here. ._

It was so dark throughout the house that Dean could literally be following right behind you and you’d never know. The thought of his dead black eyed stare as he silently flanked you, made you want to scream for some reason, and you took the stair so quickly that it was a shock you didn’t fall down.

Feeling around the dark house, you found the front door relatively easily, and tried the knob to find it locked. _I am fucking trapped in this looming coffin. ._ _God help me_.

A little sliver of light caught your eye from the direction of the kitchen, and you instinctively moved toward it realizing with a catch of your chest that it was a knife. A large kitchen knife was just laying on the counter, seeming to magically glow with it’s own light.

After a moment of deliberation you gingerly picked it up, but as soon as the cold handle hit your fingertips, the kitchen lights came on.

You froze staring at the knife in your hands. . it had been a trap.

A deep clearing of a throat sounded somewhere behind you.

 _Fuck_.

**Notes for the Chapter:**

> Yep, I lied to ya. There are gonna be 5 chapters, and the next is the last :) I had to break it up for an ending worth our time! 
> 
> As always, comments and suggestions are welcome ~ Dean fucks you in the next chapter, I have to tell you that because of how long it has taken xD I know the wait is killing me too, but it's gonna be a good one.
> 
> Hope you enjoyed and thank you all for reading! Love always ~ Come kink with me on Twitter @DirtyMind_Girl


	5. Make The Bitch Sing

**Notes for the Chapter:**

> Picks up right where we left off :) SO sorry for the month long wait lovelies. You've all been wonderfully patient for this last chapter, and I hope it's everything you've ever dreamed! <3
> 
> ~ Dean possesses original Demonic powers that I've created for this chapter so keep an open mind ;) Also something of note, is that the reader is exceptionally afraid of intimacy due to past experience. Prepare for some unexpected Winchester feels. . Sorry.
> 
> Seriously, this is such a dark chapter -- enjoy guys, loves <3

“Hmmm. . . like a mouse to sugar,” you still hadn’t turned around, the fear was immobilizing you, “so I don’t fuck you after you beg and scream about it, and this is how you say thanks? What were you planning on doing with that, huh? Killing me?”

It was a trap.

“N-no,” you stuttered, still too afraid to turn, “It was just gl-glowing so I -”

“Save it.” he cut you off, “Look at me.”

“Dean please I -”

“Turn around!” he boomed, startling you enough to drop the knife. It clattered to the linoleum. Footsteps drew near, the sound making your knees jelly sending you slumping to the floor as you gripped the counter for support. “I knew I would regret not tearing you in half last night, fuckin’ knew it. Better late than never right?”

He came to a stop right behind you, “Get up slut.” 

“No!” it was a desperate cry. This wasn’t fair! He tricked you into picking up the knife so he’d have a reason to hurt you, but then again, why expect much else from a demon? The thought gave you enough courage to detach from the counter and lunge for the knife that had landed a few feet away.

It scraped and clattered against the tile at your feverish fumbling but somehow you managed to get a grip and spin around to face him, sitting on the floor with the knife extended from your shaking hands.

Dean seemed almost bored in the way he assessed your tearful huddled up form on the floor, as if he expected nothing less, but there was a certain glitter going on in those intense eyes just below the surface. One that told you this was about to go from bad to worse.

Using the nearby fridge for support, you managed to clamber up from the floor without lowering the knife or taking your eyes off of the watching Demon. He was stoic.

“Let me out of here.” you brought a hand back to wipe your nose while Dean just smirked at you. This time you yelled, “Let me go!” it seemed to echo in the kitchen, but he didn’t flinch.

“You gonna cut me sweetheart?” you swallowed, glancing around the kitchen for anything that might help you. _Anything_. Of course there was nothing, and the big man took a deliberate step forward, “You think you can kill me with that, little girl?” a little sob busted from you chest while your vision blurred.

No you didn’t think you’d be able to kill Dean in a million years. . with anything. You felt just as helpless _with_ a weapon as you were without. Dean's mood seemed to be darkening,

“Just let me go.” you said through your teeth, “This doesn’t have to end bad. .” _the only person this is going to end badly for is me. ._

“Then what hmm?” he asked as if you hadn’t said anything, “What happens if you do happen to get a good poke in with that thing?” you took a stuttering step away when he moved forward again, “You just gonna. . walk right out of Hell?”

_Oh no. ._

 He grinned, knowing he’d won already, “Ahh didn’t think of that did ya? No see. . the only way out of this place is me. I die, you rot down here,” another step forward,

“In this corpse of a house.” another step, “All alone.” he was almost touching the tip of the blade now, “For all of eternity.”

Your back hit the fridge and Dean crowded in slowly,

“D-Dean -”

“You know me though. .” he leered, “Always up for a good wrestling match - after all I think I might’ve gone too easy on you last night. Whaddaya think babygirl?” the tip of his tongue peeked out from between his teeth, 

“Do you deserve to be punished slut?” another sob punched out, and your weak knees were bowing inward as you gazed pleadingly up at the hulking Demon.

“I - I didn’t mean to. . don’t whip me again I’m sorry -”

“Whip you?” he cut you off with a genuinely amused laugh, still standing at the tip of the knife.

It would be delusional to think you had any control here though, he was simply keeping that short distance because he wanted to, not because you were making him, 

“Oh no, we’re way past that. ‘Sides, I’ve been dyin’ to tear up that tight little pussy since day one sweetheart. Now you’ve just given me a reason. .” your blood ran cold,

“Wh-what?” it was a quiet whisper,

“You heard me baby,” he licked his lower lip and raised an eyebrow, “you’re gonna see first hand how I fuck bad girls.” you dropped the blade at the same time your knees gave out, and you hit the floor in a heap of trembling girl. 

“No, no don’t hurt me!” once again you were sobbing before this monster of a man. You curled backward into the fridge, staring at his heavy boots through tear-blind eyes,

“Please I’m sorry Dean - don’t hurt me."

The big man only squatted down in front of you, hands clasped casually between his knees. He had a small closed lipped smile on his face, but what he said next erased all traces of kindness,

“Oh sweetheart I’m not gonna _hurt_ you. .” you sniveled and strained yourself to hold in loud sobs, praying to God or whoever could see this that he would show mercy. How foolish.

His next words were spoken softly with the tilt of his head, “I’m gonna fucking _ruin_ you.”

You wailed desperately, “What about last night? I th-thought. . .” honestly you didn’t know how to finish that sentence and the both of you just sort of let it peter out.

_I thought what? That he liked me? Please. . he’s beaten me, tortured me, and sprayed me with a fire hose._

“Whatever you thought, it was wrong.” he sneered, “It’s all part of the game baby, this ain’t a fairytale.” with that he rocked to his feet to tower over you, “Get the fuck up. I’m only asking once.”

You shook your head and remained curled up against the quietly buzzing refrigerator, closing your eyes and hugging yourself for some false sense of protection.

A huge sigh exploded from your tormentor,

“Such a slow learner. .” he mused, while he watched you cry. Familiar jingling echoed subtly through the vast kitchen, and when it registered in your mind as a belt buckle, you lost it.

“Wait, wait _Dean_ no!” and just like that you were uncurling and reaching up at him like there was a chance in hell you could stop him from hurting you. He did pause, but it was only to leer at you tauntingly,

“What is it baby girl?” he chided, continuing to remove his brown leather belt with dramatical slowness, “You know what happens when you disobey Daddy, don’t you?” his theatrics had you sobbing up at him desperately,

“Oh God, I’m sorry, I’ll - I’ll get up.” you were crawling toward him on your hands and knees, reaching for the belt that he was dragging slowly through the loops,

“Oooh sweetheart, this is gonna hurt so much more than my hand. . Remember that? When I had you over my knee. . wasn’t that fun for you?”

“ _No_! No don’t hit me again, please.” you cried, only to be laughed at,

“Well you must’ve enjoyed it a little bit baby, seeing as you got yourself in trouble all over again. I must be gettin’ too lax with the rules.” you made it to his dirt spotted boots, and wasted no time in crawling right in between them to latch onto one of his long bowed legs.

He didn’t even react as you clutched his jeans and sobbed into his thigh like there was no tomorrow,

“Please, please, _please_ ,” you wept, praying to God he would show you mercy, when all you could picture happening was him beating you with that length of leather until you blacked out. “Don’t hurt me Dean, I -I’ll be good I swear!”

His jeans smelled like faint detergent with a hint of his own musk, and you breathed it in with your face pressed into him for what seemed like a long time. 

The demon let you cry and plead there for a little while longer before a strong hand tangled into your hair and jerked your head back hard enough to elicit a pained scream.

“You’re gonna be good for Daddy, huh?” he was grinning evilly, his canines seemingly more pronounced in the dim light as they shone down at you. Playing along you nodded tearfully,

“Y-yes - yes! I’ll be good for you Daddy, I swear." there was an obvious bulge in his jeans that you noticed just before he jerked you up to your feet by the roots of your (h/c) locks.

You screamed and grabbed at his hurtful hand, while trying not to think about what was waiting for you under his zipper.

“Good,” he growled into your ear, his breath burned the side of your face, “Cause Daddy’s got a nice thick, long present for you.” with that you were thrown into the side of the counter, hard enough to jar your bones and make you screech in pain.

_No, no, no, no!_

Dean was on you in a second, plastering you to the counter with his muscular body, and trailing his hands wherever he pleased.

“D-Dean,” you mewled, “ _Nooooooo_. .” the edge of the counter ground into your hips painfully as the big man kept you pinned there. Through his pants, you could feel the bulge in his jeans on your ass - his " _present"_ he called it - and the size was more than intimidating.

Especially with the way you knew he was about to use it. For violence. For pain.

Sometimes, even before this, you wondered if men realized - like, _really_ understood - just how much hurt they could cause with their intimate instrument. It could be a weapon just as easily as it could be an implement of pleasure.

In fact it could much more easily be used as a weapon now that you thought about it. And you _were_ thinking about it, because Holy Hell the thing was grinding into the back of your thigh and Dean was breathing raggedly while he forced you over the granite counter top.

That was one of the reasons you hadn’t gotten much sexual experience before all of this - only two partners and the last one was more than a two years ago - because you didn’t trust easily, you couldn’t get comfortable enough to let them in.

_Quite literally._

Of course now was no exception, which it why you were currently bawling your eyes out over the kitchen sink.

“Please!  _Please_ don’t do this. .” you sobbed, gripping onto the sink nozzle like a lifeline, when two sudden rough thrusts into your naked ass, jolted you into the counter hard enough to make your bones grate,

“How ya doin’ baby?” Dean breathed, leaning over your back to mumble in your ear, “Ready for me? Huh? Ready to take your punishment?” you sobbed so hard you couldn’t breathe,

“Oh come on now. .” he taunted, “You were a bad girl sweetheart. . what happens to bad girls?” he growled when all you did was press your lips into a line, and gripped your chin to pull your face up.

“What happens to bad girls, bitch?” he snarled, lapping at a few tears cascading down your cheek. His breath was hot on your face,

“Th-they get _punished_ ,” you wept pathetically, while trying to cant your hips away from his. He sighed,

“But you’re still trying to get away,” the demon tsked at you before bringing his free arm around to your front. As soon as his cool fingers grazed your sex you began to jerk around wildly,

“NO!” somehow the man captured your clit between his thumb and forefinger, causing you to go stock still. He squeezed it slightly and let your head drop back into the sink. “ _St-stop_ it.”

“Shut the fuck up,” he pinched your clit mercilessly and you screamed in pain, spasming in an effort to escape him, but his body pinned you firmly and there was nowhere to go.

“What’s the matter princess, haven’t I been generous? I’ve made you come - _hmm_ \- four times, and I haven’t asked for anything in return have I?” you shook your head sniveling miserably.

Sure, last night you jerked him off, but he didn’t ask for it and you only did it so he wouldn’t rape you. . _that sure worked out well_.

“So I think I’ve earned a little something haven’t I?” he pushed on your nerve bundle hard enough to make you gasp, “The right to tear up your little pussy. Yeah, I think so baby.”

Without warning a thick finger slipped down and crammed into your opening - no prep, no care - and the pain made you scream, “Just one finger and I got you screamin’. It’s gonna be a long night for you sweetheart.”

“Please Dean, please stop - _ah_ \- you’re _hurting_ me." you squeezed your thighs together, wailing when he added another finger to start thrusting,

“No see, I fell for that shit last night. And what did you do?” he pounded those two thick digits into your dry core, “As soon as you were alone you found something to kill me with, how’s that for a thank you?”

“I-I’m sorry I wasn’t going to stab you I swear." he chuckled and withdrew his fingers sharply, groaning at the way you yelped. When you felt him pull back to work his button open, you redoubled your efforts to escape. Desperate for some distance before he got his pants off,

“No don’t do it -  _Dean,_ I’m begging you!  _Ple-e-ease._ .”

However when his zipper sounded, you went completely limp over the sink, weeping miserably at the pain you were about to go through - emotional and physical. _There is no getting out of this. It's happening._

“Remember that bright pink dildo baby?” he held you down by the back of your neck and cupped your sex, rubbing and squeezing in a claiming way. Of course you remembered the offensively pink pleasure toy, he almost defiled you with it after all,

“ _Y-yes,_ ” you whimpered, “Dean _please_ -”

“You're gonna be begging for that little thing when you feel what I’ve got for you - think you can take my thick cock sweetheart?” he laid it against your ass, allowing you to feel the length and girth, and outright laughing when you started bawling and struggling at the touch. “Is that a _no_? Aw sweetheart, you got no faith. I’ll make it fit, don’t you worry.”

“No! _No_ \- oh God _please_ no!” you choked on your own snot, shaking harder than you ever had in your life and shrieking in anguish when you felt him position the thick head right on your tight opening,

“Oooh, it’s gonna be a tight fit baby girl. It’s alright,” he leaned over your back again to kiss your cheek, “You can scream as loud as you want.”

The irony was in the forefront of your mind really. Here you were with this demon, who was undeniably attractive - painfully so - who was raring and ready to preform unspeakable sexual acts, yet every cell in your body was screaming " _no_ ". When honestly, had Dean picked you up in that bar instead of Crowley, you would have done everything in your power to take him to bed.

So with all of that floating around in your mind, you tried hopelessly to relax against him - to see this in a different light.

It was a lost cause, you could feel it in your soul. . because context mattered. And right now the context was, Dean was about to rape you against the kitchen sink of your long lost childhood home - he wanted to hurt and take. And goddammit, you were scared. Just so fucking _scared_.

In fact, you couldn't even stop whimpering long enough to listen to his growling voice,

“Oh I’m gonna fuck ya sweetheart, and you’re not gonna like it  - not one bit - you know why?” you shook your head, unable to think of a single word, “Cause I don’t give a shit about you . I don’t. Not about your comfort, your feelings, your life. I don’t give a shit.”

“Please don't hurt me Dean," you whispered tearfully, bracing yourself for anything and wishing you could do more than just plead with him. Helplessness is a terrifying feeling. As if your brain was grasping at straws for some form of comfort, it landed on a lost memory you had of your childhood. Of your mother.

She was in this very kitchen, the one a demon currently had you bent over the counter in, singing her favorite song while she cleaned. It was like you could hear it then, melodic and beautiful in her lost voice, and before you knew it, the words were oozing out of your own mouth,

 _“Hey Jude. . Don’t make it bad. .”_  it was strange. You knew that as you were singing, but as some people might rattle off prayers in their last moments of control, your subconscious chose to sing. _“Take a sad song and make it better. .”_

Dean was as stiff as his boner behind you, his fingers were locked down tight and there didn’t seem to be a muscle moving in his monster body.

The song still played in your head, your mother’s voice replacing your own and you held onto it tightly, eyes squeezed shut, mouth clamped down to muffle screams upon his entrance, and toes already curled in sickening anticipation.

Dean still wasn’t moving. .

“J-just get it over with!” you wailed. Why isn’t he moving? Just let this be over quickly. . please. Dean’s deep voice startled you, it was strangely soft yet urgent,

“What. . how the fuck do you know that song?” you sobbed, wishing to hell that he would stop toying with you.

“Please Dean, I’m _begging_ you just please -”

“No.” he growled through his teeth, squeezing the flesh on your hips well past the point of bruising, “The song. How do you know it?” it was extremely hard to say anything that wasn’t desperate begging, with his cock still pressed up against your quivering opening, but after a couple deep breaths you somehow managed,

“M-my mom used to s-sing it when she was -” an involuntary sob cut you off, but Dean waited, “when she w-was in here. Th-the kitchen I mean.” the man stayed quiet, “It calms me down sometimes.”

“And now?” he asked,

“N-no,” you whimpered, more tears filling your eyes.

“Why not?”

“Be-because I’m too _scared_ ,” you wept, “because I know y-you’re gonna hurt me - _please_ don’t.” a low hum mingled with his soft exhale as he took in your words. Of course you had no hope at all, you were still tight as a bow waiting for an excruciating thrust.

When you felt him shift slightly, a shrill whine drug out of your throat,

“Shut up,” he bit, flexing his fingers on your skin. An idea much like the one you had last night popped into your head. _Maybe if I get him off some other way, he won’t rape me. ._ So you said,

“Dean,” he grunted, “I’ll. . I’ll do _anything_ , just please - not this. S-something else. . God just _please_ , not this.” still the demon was quiet, and you bowed your back to the side in order to chance a look behind you.

Dean was still holding onto your hips, still positioned at your entrance, but the man was staring at your face. . his expression unreadable, but like nothing you’d ever seen on him before.

Green eyes flashed restlessly between your ass and your eyes, and you watched as he shuffled, licking his lips uncertainly, before releasing your waist and taking a small step back.

_What is going on. .?_

“What the fuck is going on,” he growled, shaking his head at the floor like he was trying to get something out. You however, wasted no time to figure out what was banging around in the demon's mind.

Instead, you twisted and dropped to your knees before him, with you back pressed against the lower cabinet in front of the sink. Dean’s eyes snapped to you, hooded and dark while you focused all of your energy in not looking below his waist.

Which was difficult seeing as it was just above eye level for you, and his erection had such a presence that it was all but verbally demanding attention.

At this angle, Dean came off impossibly more intimidating - he towered over you more than usual, and when he stepped forward again, he raised his chin to look down on you dominantly.

There was still something off about him though. If a demon - especially one as menacing as Dean - could appear shaken, that’s what he was. As if something you did, cracked his confidence a little bit.

_It couldn’t have been the song could it? Why would a Knight of Hell have a lingering soft spot for the Beatles?_

“Well?” he rumbled, “Either let me fuck your mouth, or I’ll fuck your pussy. Your choice.” your lip trembled even before you lowered your gaze, but you actually whimpered when your eyes landed on his cock.

Sure you’d seen it before, but up close and personal like this was something different. Now you could see clear as day how thick it was jutting from his unzipped jeans. . how _long_ it was.

Despite the lapse in action, Dean was still fully erect and ready for action. _Jesus Christ that’s the biggest dick I’ve ever fucking seen._ What Dean didn’t know, but would likely find out in the next five seconds, was that you’d never given a blowjob in your whole life.

 _This is better than rape. . better than rape. ._ Even though part of you felt like this still might count. _It would be less painful._

“Okay. .” you whispered to yourself before tentatively reaching out for him. As soon as your hand closed around it, the thing jumped. It _jumped_. “Oh!” you gasped, drawing back frightfully to look back up at him.

He was smirking, except this time it wasn’t mean or taunting. . the smile looked sort of _genuine_ , and it was. . well shit it was actually kind of _pretty_.

“Jesus princess, you sure you’re not a virgin?” instead of answering him, you gulped and leaned back up on your knees to take him back into your trembling hand. This time when it twitched, you didn’t pull back.

The head appeared swollen and red with need, so following instincts alone you leaned forward and licked it, “Mmmm,” he hummed, rocking forward slightly. Again you licked, this time coaxing and oozing dribble of pre-come out of his tip.

Swiping your thumb across it, you smoothed the wetness over his thick shaft, trying not to think about how something that large would fit inside of you. Your hand didn’t even wrap around it all the way.

 _That is a hell of a lot bigger than that fucking dildo._ With the fear of penetration fresh in your mind, you sat up higher on your knees and opened wide to take the tip in your mouth.

Again he groaned, but when he rocked forward slightly you gagged and pulled off of him, totally beside yourself with how this would work.

Dean seemed to grow bored with the constant stroking that you were trying to distract him with, and reached down with a sigh to tap your cheek,

“Open.” A tear spilled out and you pumped him harder, desperate to appease. While he did give a pussy-clenching groan, it only satiated him for a second,

“Come on, open up.” he sharply tapped your cheek again, and with a shuddering breath you did as he asked,

“ _Wider_.” a sob cut out, but you obeyed and he swayed forward to push himself in.

It was a shallow thrust, “Now suck.”

Closing your lips around him, you tried to do as he said. . you really did. Maybe it would have been easier if he wasn’t so scary, or you weren’t trying not to break down, or if he was of average size, or if you had even the slightest clue what you were doing.

Whatever the problem was, the result was still the same: you were giving perhaps the worst blowjob of all time.

Dean filled your mouth and blocked your airway. Every time he thrust forward even slightly, you gagged like a model on her toothbrush. When his hands tangled into your hair to force himself deeper, you dug your fingernails into his shaft by accident. . it was surprise that you didn’t get backhanded for _that_ shit.

It went on like this for maybe ten minutes before Dean had enough. The ninth time you pulled off for air, you couldn’t help but whimper a couple times, still hanging onto his thick member like a support bar.

“Oh for fuck’s sake.” Dean lifted you from under your armpits, causing panic to shoot through you with that action alone.

“ _No_!” you cried, pushing away from him and into the counter, “No, I’m _sorry_. .” you pled,

“Calm down -”

“I’ll do better I swear to _God_!” it was frantic, and you tried to get back to your knees, but Dean held you fast by your arms. “Please, I _swear_ \- I’m sorry, I can be better.”

“Shut the fuck up!” he roared, shaking you roughly. His grip was painful on your arms, but that wasn’t why you were sobbing. _He's gonna fuck me now._ You were about to be raped because you couldn’t suck him off well enough.

_How pathetic._

Sagging in his grip defeatedly, you reached down to cup your sex with both hands, crying in earnest when he growled.

“Dean please, let me try again. .” you sniveled, curling away from him with your eyes squeezed shut.

“No -”

“Please!” you burst, but one of his hands snapped to grip your chin and he tilted your face up to his.

“Open your eyes .” again your name on his voice sent tingles shooting through your veins, but you were on another plane of existence now.

One where all your body knew how to do was tremble, where all your voice knew how to do was beg,

“ _P_ - _please_.”

If it wasn’t for his strong hands you would have crumpled back to the floor. “Last chance sweetheart. Look at me.” whimpering, you managed to crack them open, only to wish you hadn’t when you took in his black orbs.

“ _No-o-o_!” you sobbed, trying to pull out of his grip, but he tightened the hold on your chin.

“I want you to do something for me,” he purred almost gently, “If you do it, I won’t hurt you.” you blinked, trying to calm the white hot fear that kept striking from staring at his inhuman eyes,

“Y-you won’t _fuck_ me?” you whispered disbelievingly, and he barked a laugh,

“I never said that.” his lips pulled into a frown when your tears flowed harder, “Shh. .” you flinched when he wiped some away with his thumb, “But I won’t hurt you.” Your teary (e/c) eyes flickered down to his intimidating member. . Good luck with that, stud.

“W -what do I have to do?” something humiliating no doubt. Even though his features relaxed, you were totally expecting him to say something abhorrent like “just turn around and finger your asshole while I watch” so what came out instead caught you off guard,

“Sing.”

You sputtered, “Wh- _what_?”

“Sing for me,” he almost whispered it that time, and you weren’t sure if when his green eyes came back it was on purpose or not. “I want to hear it.” you swallowed at how close his face was to yours,

“What do you want me to sing?” you asked just as softly, and he gifted you a small smile, finally releasing your chin,

“You know.” his eyes flitted over your features while you took a few deep breaths, and began the song in a quiet trembling voice,

 _“Hey Jude. . Don’t make it bad, take a sad song and make it better. .”_ your voice was never really great, but now with the fear and quaking it sounded borderline terrible.

Dean however gently closed his eyes as you sang, absently caressing your hips with disarming gentleness.

 _“Remember to let her into your heart, then you can start to make it better. ._ \- OH!” you gasped and startled when his warm lips touched your neck,

“Keep going,” he growled on your skin and with much determination you did,

 _“Hey Jude, d-don’t be afraid. .”_ you hardly even sang that part, it was more of a whisper as he trailed gently kisses along your neck to your collarbone, then across your throat, and back up the other side to your jaw.

Stubble was scratching at your skin and causing a burn where it touched, as well as a different kind of burn where you wanted it to touch.

“Louder baby,” his lips were butterfly light on the corner of your eye, making you shiver with something other than foreboding.

Big rough hands slid up to your chest and cupped both breasts firmly, just before he brought that amazing mouth down to gently lick and suckle on your nipples.

Punching breaths might have ruined your song if it had sounded good in the first place,

 _“And anytime you feel the pain, hey Jude, refrain. . Don't carry the world upon your shoulders,”_ you panted between measures, squeezing the counter until your knuckles turned white when all you really wanted to do was run your fingers through his full hair like you had only hours before.

“So pretty sweetheart. .” you weren’t sure whether that husky porn voice was talking about the song, or your body, but you whimpered needily and pushed your chest up further to his face.

Your sex throbbed, but you didn’t dare do anything about it - or ask him to do anything about it for that matter.

The song was at the "Nah Nah’s" and they really sounded more like moaning whines,

 _“Nah nah nah nah. . . nah nah nah nah n-naaahh. .!_ ” his chuckle vibrated a nipple and made your face heat up, but when Dean abandoned your chest and crowded up into you, a little spark of fear came back.

The former Hunter was so big that his body blocked out the dim light of the kitchen and cast you into a shadow that made his facial features appear downright sinister. . or maybe he just was sinister.

“Hey don’t quit singin’ sugar, we were just getting to the good part.” your eyes fluttered at his hot body pressed against you, and your lips trembled at the innuendo - both for very different reasons. Nevertheless you kept up the old song,

 _“Hey Jude, don't let me down. . You have found her, now go and get her_ ,” a startled yelp burst out when his rock hard thickness nudged between your thighs, and you began to protest when he hiked your leg up over his hip,

“No - Dean no -”

“The. Song.” he snarled, “Fucking sing for me, slut.”

 _“R-remember to let her into your heart,”_ you sobbed once, _“then you can start to make it better. .”_ the tip of his cock traced up and down your swollen pussy lips over and over again, while one hand kept your leg crooked up, and the other kneaded your ass generously.

A breathless moan escaped you when he increased the pressure of his rubbing, catching slightly on your opening on it’s way back to chatting with your clit. It felt heavenly.

So much so that you forgot to keep the song up.

“You want me to fuck you, is that it?” he was so much taller than you, that instead of nipping at your earlobe when he said that, he nibbled the crown of your ear - and even then he had to bend low.

“I - I,” you stuttered before continuing the song a tad frantically, _“So let it out and let it in, hey Jude, begin. You're waiting for someone to perform with. .”_

This time when his tip hit your clit he paused there and ground into you, circling his hips and trailing his lips toward your gasping mouth,

“Fuck. .” he groaned, moving even closer to you. The pressure on your pleasure nub increased significantly with the movement,

“Aah. .” the song just sort of poured without melody along your sighs and suppressed moans, _“And don't you know that it's just you, hey Jude, you'll do - the movement you need is on your shoulder_ \- Ah oh God please. .” his own deep rough moan sounded right into your ear, and shot straight to your throbbing pussy.

You were unbelievably close to coming on the head of this man’s dick - the same one that you were begging for mercy from, just minutes ago. You should’ve cared more.

 _“Hey Jude, don't make it bad, take a sad song and make it better. .”_ it took you a moment to realize that the demon himself was just barely singing the repeat chorus along with you, and for some reason that made your chest hurt.

Still you kept going, chasing the orgasm with the lyrics with this uncanny theory that he was going to give it to you with the last line of the melody, _“Remember to let her under your skin. . Then you'll begin to make it better - better - better -”_  

He roughly rutted into your clit with each repeat of the word, and just like in the song it built until you were basically screaming it, and with one last _“Better!”_ Dean’s pressing and dragging on your nerve bundle had you coming.

 _Hard_.

“Oh _fuck_!” you cried, hips fluttering against his, “De-” he cut you off with his mouth smashing against yours. Full lips assaulted your climaxing senses, and you panted into his mouth while you were squeezed tightly up against his body.

The kiss was the opposite of your orgasm, it was gentle and sort of passionate as you rocked through wave after wave of pleasure, and

Dean just kissed you and tongue fucked you through it. As you began to come down, the demon shuddered against you, sliding his member through your slick lips at a breakneck pace but still managing to remain exterior.

The hot liquid sensation told you that he too had come from the strange grinding, and as your orgasmic pulses began to die down you realized that Dean had stopped kissing you - instead his forehead was propped up against yours and when you opened your eyes he was already staring with greens that looked pure as emerald.

“Damn. .” he breathed, swollen lips brushing yours lightly. Your sex was still tingling enough to give you goosebumps and his wilting erection was still impressive against your inner thigh,

“Thank you,” you whispered nervously. While it felt like something needed to be said about the lack of vaginal tearing you just endured, it was a thin sheet of ice to walk across seeing as you were technically still his fuck toy for however long he kept you.

_Perhaps forever._

But the two of you - tiny human girl and over-sized demon - stared at each other for a moment, breathing heavily and shaking visibly. Dean’s hands were still gripping your ass cheeks, and your leg was still squeezing his hip, but the way Dean was gazing at you chased away all opposing thought.

His eyes were wide and bright, his mouth slightly agape, and his head was tilted to the side with his forehead on yours. . he was studying your face like you were some new-found species of flower - like he wasn’t sure what to think of you all of a sudden.

It was very likely that you were staring at him in the same way.

_If he touched me right now, would I die from his poison or would I kill him with mine?_

A sharp inhale sucked through your throat when the man’s mouth angled slightly toward yours again. . his eyes flickered from your glistening (e/c) eyes to your swollen red lips, while he hung there in the space between another kiss and his uncertainty.

It was an odd look for the demon. Uncertainty. Your throat bobbed with a thick swallow, and his pupils seemed to dilate with the movement of your lips. Your voice was a wisp of what it used to be, so soft that it didn’t break the somber moment at all,

“Hey Jude, don't let me down. You have found her, now go and get her. Remember to let her into your heart. . Then you can start to make it better. .”

That last note trailed off into eery quiet while Dean gazed at you through unreadable green orbs. But there was no menace, no anger, and no arrogance in the way he was watching you. It was almost as innocent as if he just wanted to see what you’d do next.

So you spoke again,

“What is happening. . ?” Dean held eye contact as he gently shook his head. He seemed at a loss as well, but his pink tongue darted out over his bottom lip, catching your gaze, and he leaned forward.

You fluttered your eyes closed for a kiss, wantonly pressing into him, while your fingers kneaded the rough material on the arms of his jacket. But just as that first tiny hint of velvet brushed you, a horribly familiar voice broke the moment quite glaringly,

 

“Why am I not surprised?” both you and Dean startled at the sudden voice sounding from behind, but Dean immediately took on irritation and sagged with a harsh sigh,

“Not a good time,” he growled, just barely glancing back. You couldn’t see around your big tormentor, but you knew that voice as soon as it spoke, “What the fuck do you want Crowley?” you shivered at the English man’s presence, and feverishly made sure every inch of your skin was covered by Dean. 

“What do I want?” he repeated, “ _Hmmm_. . well what I wanted was for this little tart to be your bloody victim, not a lucky lover, but I suppose the fault lies with me. I should’ve known. . leave it to you to be bewitched by your prey.”

Dean’s green eyes hardened at the suave man’s words and for a moment you were afraid that his anger was directed toward you, but Dean peeled back from your clammy body and left you completely exposed to the smartly dressed Scottish man.

“Wait Dean. .” he gave you a sharp look that reminded you of the first time you met him. That look meant “ _another sound and there will be pain”_ you shivered and sort of mourned internally at the loss of such a gentle hand.

Crowley though, winked at you after raising his brow in appreciation at Dean’s semi peeking out through his unzipped trousers. It made you blush, but also feel crawly. With a huff the big demon buttoned up and squared his shoulders gruffly.

“Darling, you look better than I hoped you would.” the Scotsman addressed you and it made you want to gag under his scrutiny, praising the Lord when Dean took his attention again,

“Okay let me rephrase then, dickwad.” Dean spat, turning away from you completely, “What are you _doing_ here?” Crowley squinted for a moment,

“Besides standing utterly disenchanted with your work thus far?” Dean glared, and Crowley smirked, “I’m here to kill the damsel, she truly seems to be having the opposite effect than we hoped, has she not?” 

Dean’s fists clenched but his voice was dead low, and neither man paid you any mind as you backed to the far corner of the room.

_Kill me? No Dean wouldn’t let him do that right. .?_

“The Mark is fine Crowley.” the tailored man took a step toward Dean, ducking his head low like he was studying the seething man,

“Is it?” he prompted, “Forgive me if I’ve been mislead, but from what I just popped in on, it appeared that you and Ms.  were just about to. . . make _love_?”

Your eyes bugged, and Dean stayed quiet while Crowley’s sharp eyes flickered up over to you standing a ways behind Dean,

“I’d say the Mark is _flummoxed_. Not fine.”

“So you wanna kill her?” Dean questioned nonchalantly like you weren’t even in the room,

“Don’t fret Squirrel, I’ll get you a new toy,” Crowley sneered, “there won’t be a glimmer of difference besides maybe two testicles and a shaft. You know, to take away the temptation.” he raised his brows,

“Unless you're into that.” your gaze flitted back and forth between the two Demons, wondering what the hell was about to happen to you.

_I’m dead. ._

“Fine.” Dean’s word hammered a nail into your chest, and actually elicited a gasp, “Go ahead, she’s been nothin’ but a pain in my ass anyway.”  

“What? No!” you cried, stumbling back toward the far corner of the room. When Dean turned, his expression was devastatingly passive. He merely glanced at you before stepping out of the way to make room for the casually approaching Crowley, 

“Dean _no_! What - what about. . .” he was watching the small man in the tailored suit with an indifference that shattered your hope - and you heart oddly enough.

The King of Hell leaned in from about two feet away with a sarcastic apologetic look,

“Apologies my dear, you come expecting torture and instead are given underwhelming orgasms. . we’ve all been there.” he only smiled tightly when you pressed further back into the corner, “Brace yourself darling, this might burn a smidge.”

There was no holding back a scream when he reached for your face, but a huge collision erupted before he managed actually touching you, and the smaller man was slammed into the wall. Leaving Dean, rippling with rage in front of you. . of course you naturally shrunk back from him.

“Go.” he growled, black eyes flashing with a hate that you could only hope wasn’t directed at you,

“Now Squirrel, is that really a way to treat your King?” Crowley was fretting over his suit, and you were backing out of the room, watching Dean approach him with more alarm than the King himself.

“I don’t work for you. . .” and that was as much of the conversation as you heard before you turned and flew to the base of the staircase.

 

You took the stairs two at a time, vaulting up against the railing on the wall as you scrambled frantically to the non-existent safety of your childhood room. You couldn’t help the feeling though. . and that’s what pushed you through the doorway and flung you into the bed.

That childish hope and familiarity had you burrowing under the covers as the demonic fight raged downstairs. Growls and roars drifted up the stairs, you swore you could even hear smacks of skin hitting skin all the way from the kitchen.

“Oh _God_ get me out of this. .” you wept under the covers. They still smelled a little like sex, but for some reason the hint of Dean was comforting. _He is saving me right? Right. But why. .?_  

While you were grateful that he didn’t let the smarmy Scottish man turn you into a charred log, you were extremely wary of the demon’s reasoning behind it all. But thinking back to that kiss. . that moment just before Crowley appeared. . you knew deep down that you would have given Dean anything he asked you for right then.

 _Anything_.

Perhaps that was the scariest thing of all. The noise went quiet, silent really, and you strained your ears to hear anything that would give away the victor, or let you know you weren’t alone. Heavy thumps on the stairs hit your ears and seemed to resonate through the whole house, they were slow, methodical, and coming for you.

With a frightened whine, you tightened the blanket fort around your body and curled up into a little ball of quiet tears. The footsteps were relatively silent once they hit the hallway, so when your assailant finally spoke it startled you enough to make you yelp,

“Sweetheart, are you hidin’ from me under the blankets?” _Dean_. Perhaps you weren’t as relieved as you should have been.

Cowering under the sheets as he approached, you felt very much like the little girl that used to inhabit this room. Oh Dean was going to get you alright. . but for some reason the little fort you’d hastily fashioned made you feel like he couldn’t.

If only for a moment you felt a little safe. And it was only a moment, because Dean was tugging at the sheets firmly, unrolling you like a stern father might a disobedient child.

Dean had this sickening look of mock pity on his face once he uncovered the tearful little puddle you really were right then,

“Aw, baby girl. . someone looks afraid of the boogeyman." He glanced around the room dramatically, “Does he want in on the action too?” you hiccuped miserably, “He can have your pretty little ass. . I’m more of a pussy man myself.” his smile only grew when your face crumpled,

“Come on sweetheart. . I thought we had a moment out there.” he pouted dramatically, “I saved you from the big bad King of Hell, that deserves a good fuck, don’tcha think?” your breath broke on the way in, and even though you knew the answer you still tried to ask,

“Are you. . are you gonna -”

“Shh. .” he brushed a few strands of (h/c) out of your face, tucking it behind your ear gently, “Quiet baby, there’s nothing to be scared of.” this was a far cry from the man you had become acquainted with,

“Why did you save me?” you whispered, gazing up at him from the blanket pile to see his lips twitch,

“M’not too keen on people taking my property,” he hummed, stroking the side of your face, “I’ll fight for what belongs to me.” _does that mean he cares about me?_ You swallowed before whispering,

“I - I’m not property Dean, I don’t belong to anyone.” you said it in such a way that it wasn’t accusing or defiant. Instead it was only a fact. _You can’t own people._

When he nodded, he did so gently, and thoughtfully.

“If that’s what you need to believe, princess.” then he cupped your jaw, “Come’ere.” with shaking limbs, you managed to sit up on your knees and bring yourself to eye level with his chest.

“Did you kill him?” he chuckled, stroking the spot just below your eye,

“Does Batman kill the Joker?” that brought you up short - what a dorky thing for a Knight of Hell to say - and then you saw it.

Humanity.

For a moment you weren’t looking at Demon Dean, no, a split second passed where you were staring into the eyes of the real Dean Winchester.

It was beautiful. . and sadly fleeting. So you tried to bring it back,

“Are you calling yourself Batman?” you whispered timidly, fingering the fabric of his black t-shirt, and he leaned down to be level with you,

“Oh sweetheart. . In the state I’m in right now,” he rolled his eyes in a pondering fashion, “I’d make Batman my bitch.” _why was that hot?_

Goosebumps rose all along your naked body due to both the chill in the room and the company you were keeping, and you shuddered at the small smile playing at the corner of Dean’s lips.

He groaned low when you ran a hand up his chest, and let his head fall back when your fingers pulsed on the hard muscle there.

“Got somethin’ on your mind little girl?” he groaned, capturing your wrist lightly to lift it up to his face before looking you dead in the eyes and sucking two digits between those sinful lips of his.

Well if you weren’t in the gutter before, feeling that soft pink tongue work around your fingers while he suckled, sure tossed you right the _fuck_ in. His eyes were dark, though not black, and he took up his other hand to delicately circle a peeking nipple, causing a grin to play at his lips when you exhaled involuntarily.

“Dean. .” the way he was acting was giving you a false sense of security. It _was_ false, right? “I don’t do this very often.” it was a relief when he didn’t tease or play games, instead he popped your fingers out and simply said,

“I know sweetheart,” before gently tweaking a nipple. _Oooh God that feels nice._ . But your eyes fluttered open when he kneeled down onto the bed and shrugged away his jacket and flannel. He was so close that you had to sit back on your heels to keep a slight distance.

Dean didn’t seem to approve of that, judging by the way he peeled off his shirt and jerked you closer by the hips. _Muscle._ Oh fuck there was so much of it. Hot, hard, warm. . Smooth, soft, and disarming. .

You breathed him in greedily, just the smell of Dean - gunpowder, whiskey, and fucking _man_ \- and found yourself saying something that was both obvious and compromising.

“I - I’m _scared_.” you whispered into his thrumming chest, “Dean, I’m afraid of you.” a low him followed by another,

“I know.” he nuzzled into your neck to press his lips down firmly along your pulse point and you whimpered, “You should be.” with an alarmed whine you stiffened, but he did nothing other than hold you tighter and continue his pussy aching kisses down to your shoulder.

As if he heard the silent cries of your traitorous sex, his thick fingers were suddenly calming it with tender circles that made you want to pant. He was being gentle, which was strange, you expected him to roar up those stairs and mount you like the champion he was for defeating Crowley. .

However sweet this demon seemed though, to allow the feeling of safety would be idiocy.

There was nothing safe about Dean at all. And this was only the feeling of consent - not the real thing. There wasn’t a doubt in your mind that the culprit of your racing pulse and slickening folds didn't really give a damn about that trivial requirement at this point.

If you denied him now. . You shuddered. There would be no denying him now. Not with that familiar hardness poking at your belly - _hello there Mr. Friendly._ . you almost laughed, knowing that Dean’s manhood was much closer to a

_Mr. Intimidating._

_Dr. Threatening._

_Gen. Pain. ._ . _Lord help me._

“Why the tears?” you startled a fraction, not even realizing that there had been tears until he was wiping them from your face, “M’not hurting you sweetheart. .” you avoided his eyes with a flaming face,

“Not yet.” his harsh sigh made your skin chill, and you naturally shied away from him which seemed to make his mood darken further.

_Oh shit. No, no, no -_

“Lie back,” it was rough and almost tired sounding,

“D-Dean _please_ -”

“Don’t start that shit with me princess, lie the fuck back.” his venomous tone made you flinch, and with a deep quaking breath you inched backward, taking your legs out from under you.

“O-okay but. .” the look on his face made the sentence trail. He appeared ready to attack if he heard the word “ _please_ ” come out of your face one more time. Which of course made it harder not to say it. When you finally made it to your back, Dean seemed to tower over you on his knees.

Even though he was still trapped in his low hanging jeans, that bulge was so prominent that it might as well had been staring you right in the face. Both of you knew full well that you were laying there with your thighs clenched tight, completely at his mercy. . and while it was terrifying for you, it no doubt pleased him.

Although there was actually a troubled look on his face.

“Open those pretty legs and let me taste you baby girl,” you gasped and his eyes flicked up to you from your sex, “you seem to like that.” as he lowered down to his hands, he held eye contact and as if they had a mind of their own, your legs inched apart for him.

And as soon as he gave you a little lick, you were glad they did. He grinned in that stupidly sexy way that made you want to scream,

“Thought so,” a little kiss to your mound made you jump and squeak, “Yeah you like me kissin’ your cunt huh baby. . like my tongue on your pussy? _In_ your pussy? I know it sweetheart - you’re fucking  _drippin_ ’ down here.”

“ _Oh_! Oh _shit_ Dean!” he smacked a loud sucking kiss right on your clit and chuckled darkly at the way your hands flailed about. Your sex was throbbing - no _pulsing_ \- with need, and every cell in your body seemed to be shaking with both desire and fear for this man.

 _This_ _demon_. With a naughty wink he clipped,

“Hang on baby,” and dove in. A heavy arm draped over your hips to stop you from bucking when his hot tongue speared your swollen sex. It nudged in, plunging deep inside your wet channel and making you gasp and whine.

He sighed hot and heavy on your pussy, groaning with enough passion to send vibrations all the way to your spine. _Holy Hell._ . Strong fingers flexed - one on your hip and one on your breast - pinning you down and hopelessly turning you on, when you felt something other than his tongue begin to nudge at your opening.

He swirled his soft sloppy spear up to your clit, punching a porn-worthy groan from your lungs, when it hit you. _Both of his hands are occupied so what it pushing inside of me. .?_ With a frightened gasp you tried to sit up straight, but Dean slammed you back to the mattress with a borderline roar into your quivering folds.

You sobbed in renewed fear, thrashing at the suckling pleasure he wasn’t letting up on,

“What _is_ that?!” you pulled at his hands, twisted your body, and tried to close your legs, but whatever was attempting entrance was succeeding. And it felt significant. “Please Dean, what _is_ that!?” hot tears soaked the mattress beneath you, as the mystery object pushed deep.

It was painless though. . in fact it felt _good_. Dean gave you two more strong licks before coming up for air, and telling you in a panting voice,

“Shh, calm down sweetheart,” you didn’t, because that thing was pulling back out of you again and there was a delicious drag, “It’s only my Darkness baby.” _Only my Darkness? What the fuck does that mean?!_

“No - _ah_! What is that?!” you screamed again, when it plunged deep with a little more vigor that time. There was a laugh in his voice,

“Angels have Grace right?” you mewled, trying to see what was slowly fucking you, only to see nothing, “Well Demons get Darkness. . relax and feel it. M’not gonna let it hurt you.” now that you focused, it didn’t feel like a solid object at all.

More a concentrated collection of power, nudging and molding to your walls. . stretching and massaging gently at your deepest reaches.

Whispers of the power snaked up from your hips to your breasts and circled around your nipples, pulsing and kneading just like Dean’s mouth might, and when you gathered the courage to look down there were writhing black vines that appeared to be made out of a weightless air.

It was terrifying, but undeniably pleasurable. . in fact you were squirming, gasping, and mewling like a cat in heat as the Darkness wriggled against all of your pleasure points.

Dean was just beaming at you from between your thighs like a happy dog at the sight of you coming undone,

“You like that don’tcha? Knew you were a lil freak.” you were nodding hazily, meeting the tendrils of power on your breast with your fingertips to knead your own skin beside them, feeling flushed and on edge as that maddening largeness pushed in and pulled out repeatedly.

It was _filthy_. _You_ were filthy. But no morals stopped you from coming as soon as Dean touched back down with his mouth.

He sucked at your clit - feasted on it for about two seconds before you were arching your back with a raw scream, clenching down on the Darkness and coming hard enough to feel it slicking up your thighs. Dean couldn’t lap it up fast enough, but he seemed to really be trying.

“ _Ahhhhhh_. .” you groaned, jerking and tensing with each wave of dirty pleasure, “ _Dean_! Fuck! Oh my _Goooooddd_. .” finally the strange thrusting and pulsating faded away as your orgasm died down, to leave you panting and sweating on your childhood mattress.

 _I just came on a demon’s Darkness, on Dean’s tongue, in the same bed I slept in when I was seven. Jesus, when I get out of Hell, I’m going straight back to Hell._ Dean pulled in his demonic power and left your body craving it’s touch,

“Damn,” he rumbled, grounding you with his rough voice. You felt high. “that was sexy as Hell sugar, you think you’re ready to take me?” you lifted your head just as Dean dropped his pants, to reveal exactly how much he wanted you, and while there was a tingling desire low in your belly, there was also that insidious fear.

It almost made you _angry_.

 _Why can’t I just be normal?_ What a bizarre thought, seeing as any normal woman would likely be afraid to bed a demon. . but you knew deep down that wasn't totally the reason for your fear.

While it played a huge part, there was the familiar nagging in the forefront of your mind that made you want to turn tail and run from this type of intimacy. Only now you couldn’t. And that was perhaps the reason that you began to shake so violently.

Dean’s cocky expression seemed to crack a tad at seeing your breath pick up and your tears start to flow again,

“Whoa, hey -”

“Please Dean, if you’re gonna hurt me just tell me - cause I can’t tell what you want,” you sniveled and clenched your fists in the sheets, while his brow furrowed at your sudden change, “God I can’t do this. .” you whispered airly, shaking under his gaze.

Of course who you were about to let in was a lot of the problem.

Had it been some quirky little nerd, it might have been easier to let go and trust. . but Dean. . well shit he was a loose cannon. And honestly looking a lot more like a Greek God the more you stared at his naked glory.

So when he lowered to crawl over you, closing your eyes was totally out of your control.

“Hey open your eyes,” you didn’t, biting your lip to keep it from shaking so badly, but your face was crumbling, “I’m gonna fuck ya sweetheart. Now. Right here. Do you understand?” you sobbed once and managed to nod your head yes you understood.

But you were paralyzed everywhere else, ridged like a corpse mid rigor mortis. 

“I said open your fucking eyes.”

He growled, and with a desperate whimper you cracked them open to find black eyes boring down into you. Coupled with his rock solid weapon brushing lightly against your clenched thighs, Dean had you reduced to panicked tears again in no time.

He seemed frustrated.

“Shut up. Would you just shut the _fuck_ up for once?” all that came out of pressing your lips together was bursting air breaking them apart, and the demon hung his head so low that it was practically resting on the mattress beside your ear.

“Fine.” he growled, forcing your leg up around his hip with inhuman strength, “Won’t bother me once I’m balls deep in your tiny little pussy.” you clutched at his shoulders, trying to get a hold of your racking tears, but once you felt the head of him on your tiny opening for the second time that night, all composure went out the window.

“Oh - oh _God_. .” you wept, trying to unsee his onyx eyes. But they were everywhere.

“No baby. .” he rumbled huskily, “God ain’t here.” he reached down to position himself, and your whole body tensed up for a brutal entrance - toes curling in sickening anticipation - but Dean was still. Upon chancing a look up at him, he had a curious lit to his beautiful features,

“You’re terrified.” it was a matter o’ fact statement, and you only continued crying softly in answer. He nodded, and raised up on his knees to get a better look at what he was doing, before nudging in the first couple inches.

Oh fuck he was big. . you knew that already, but he somehow felt even bigger than he looked and it made you gasp and sputter,

“Ah. .” but it wasn’t a declaration of pain, not yet, in fact feeling Dean easing inside of you made your insides heat. He just looked so damn gorgeous - brow furrowed in concentration, eyes inky, lips pouty, muscles taut at the squeezing of your slick tunnel.

When the big man paused you were both panting for very different reasons, and then with one slight gaze at your strained face, Dean slammed himself to the hilt.

“ _AH_!” now that one was due to pain.

“Fuuuck. .” he groaned, collapsing back to his hands over your stiff body. Mouth open in a silent scream, your eyes bugged at the feeling of being split so wide. It was unreal. And the pain resonated deep into your core. . _I knew it would be this way_.

You didn’t even realize you were sobbing until Dean had been firmly seated inside for half a minute, the pain was so real that it made you foggy, but you were sobbing loud. So loudly that you were jerking with each breath, and it was hurting your throat,

“Jesus Christ,” Dean groaned above you again, “you’re so fucking tight baby.” _I KNOW!!_ you wanted to scream it at him, but all that came out was,

“ _Please_. .” and it was strained, he shook his head,

“Gotta move,” he grumbled, tensing up to do just that,

“NO!” you shrieked really, and the demon seemed almost startled. You flailed, one hand reaching down like you could grab the root of his dick and keep him from moving, and the other gripping his shoulder with enough force that it would make a normal man wince. “No, _no_. .” you wept again,

“Sweetheart -”

“ _Please_ no. . you’re- it hurts!” the words came out choppy and shrill, and you were so overfilled that it felt like he wouldn’t be able to move it if he tried. “Please don’t. . oh God _please_  stop. T-take it out, please... Take it out...” he seemed to have to lean down to hear you that time, the begging was so quiet,

“I. . FUCK!” his sharp curse made you flinch and whine, but the brutal punch that he delivered to the pillow by your head made you scream. “I don’t. . I don’t fucking care!” he roared above you like a wild animal.

“Dean. .” and then you said the only thing that might save you here, and it was actually true,

“Dean I want this, but - but please just be gentle. I want _you_. _You_.” he blinked at you with those black eyes and a slack jaw, flinching when your pussy clenched around him naturally, and for a moment you thought you’d lost him.

And the battle.

“You little bitch. .” he growled, circling his hips experimentally before flopping his head onto your chest, “I’m gonna count to fucking ten.” your hope sparked,

“O-okay, ten.” he hummed,

“Already at four.” you shifted experimentally, causing a primal rumble to course through the man. Wincing a little at the severe stretch, you worked on your inner muscles, clenching and moving around a little, trying desperately to adjust by the count of ten.

Even though he had already been inside of you for the better part of five minutes. Dean was making noises like he was being tortured. . maybe someday you would tell him why you might be the most difficult lay of his life. _Maybe_.

“Alright baby, here we go.” you whimpered nervously, and he planted a sloppy kiss right on your mouth before saying, “I counted to fucking twenty. I wanna feel you come now.”

“Can - can I be on top?” he sort of did a double take at the question, but you thought it might give you some semblance of control. With a deep chuckle and a shake of his head, he pulled himself out to the tip, eliciting a breathless cry from your lips, before slamming back in viciously.

He snarled, “No.”

“F- _fuck_!” you cried, arching your back only to have him move out and repeat. “ _Deeeaan_!” you cried wantonly, as he stoked this burning fire low in your belly, hitting and dragging across every spot you could ever want to feel him.

He sank deep, deeper than you’d ever felt a man and when he began bottoming out repeatedly it jarred an abrupt feeling that you had never felt during sex before.

It was blooming, _growing_ with each stretching thrust and it made you clench on him like you might explode if you didn’t.

“Oh - oh _God_ Dean - Dean - _Dean_!” you said his name over and over, and as a reward the man gave you another caught up kiss as he increased the pace into your aching pussy.

The way he growled almost _frightened_ you, in fact it did, but this throbbing ache that only grew had you canting your hips up to meet his, and spreading your legs as wide as they would go.

“Feel good baby girl? Huh? I can’t feel you squeezing on me sweetheart. . come on. . you can do it. Come for me baby.” he was panting, but not as hard as you were.

Your sex was fluttering viciously, and your body was beginning to shake with an orgasm of frightening magnitude.

_This might fucking kill me._

As soon as Dean threw your legs up over his shoulders to pound at a different angle you were done for.

Only about three more thick deep stretching plunges had your legs spasming, and your mouth gaping as you clenched down on him hard enough to make the thrusts stutter,

“Fuck me!” you screeched, scratching at his back and humping at his hips like a woman mad.

“Ugh-” he grunted, plunging as deep as he could go on the next three, fucking your orgasm relentlessly while you bayed and screamed beneath him.

As if to silence you, full lips crashed against yours, muffling your cries and swallowing your squeals so he could spear you deep one final time and go rigid with his own end.

Your pulsing sex swallowed up his heat greedily, seeming to vibrate with the remnants of your climax as if it was recovering from a trauma.

Only when you had come completely down did you realize that both of your hands were pinned to the mattress, squeezed in his tightly. . and for some reason it made your heart flutter. 

But what he said next did that even more so. Even if it was said with lingering black eyes.

Without even pulling out of your shocked pussy, Dean Winchester told you in the lowest, most claiming rough voice you’d ever heard,

“Mine. Forever. Fuck. . I gotta keep you .”

And goddammit. . it was the sweetest thing the Demon had ever said.

But those words rang true.. Permeating the air with dominance and possession.

You were his.

_Forever._

**_~~_ **

"Dean?" the car grumbled like an angry old man. Dean was pushing this 1960's hunk of metal down the highway with a determination that made your belly tight with nerves. "Dean." he hadn't answered you. 

In fact the demonized Hunter hadn't spoken a single word to you since he told you that you were his. Forever. Well except for the surprising concern when you all but limped to the bathroom after the fact. . he didn't even let you argue - the guy just scooped you up and set your limp body on the toilet like he was playing with a dollhouse. 

Then the silence started. 

After he had knocked you out for the trip out of Hell, you found woke to find yourself in this spotless classic car with only a blanket draped over your naked and battered body. _Where is he taking me? What is he planning? Is he mad at me. .?_ So many questions were bouncing around in your head that he simply wouldn't answer so when you finally asked,

"Did I do something wrong?" and he actually turned his head to glance at you, it was very surprising. So you capitalized. "Are. . you taking me somewhere to kill me?" _well that was said with shocking steadiness._ He gave a raised brow and a soft snort,

"If I wanted you dead, believe me kid, you'd be dead." _Ah, he speaks! Finally._ However the words he chose were notably unsettling. . You watched him lick his plump pink lips with a blush splashed on your cheeks, and he cleared his throat like the concerned words he was about to say actually burned coming out, "Uh, you still sore sweetheart?" 

_God with the blushing, and the tingling. ._

"A little." you whispered and earned a sideways glance, "Okay, a lot." 

"Thought so." he made like he was about to turn on the radio, and before you could think your hand flashed out to stop him. The desire to talk with Dean was clouding your judgement apparently, because the look you got sent you shrinking into the passenger door.

"Sorry." it was automatic.

"S'okay." okay now _that_ wasn't. He left the radio off. It seemed like hours before he spoke again, but it may have only been minutes. "I'm not gonna kill you, if that's what your heart is hammering about." _he can hear that?_

"Then. . what are we doing?" his normal grassy greens connected with your wide doe eyes and you flushed for a third time at his smirk,

"Well if you keep looking at me like that, we're fucking." you choked,

"I'm not -"

"Can it sweetheart," he drawled, "you can't look at a man like that and expect him not to notice. All innocent and pleading - Jesus it's all I can do not to fuck that look right off your pretty face." _Good Lord._ "Mmmm. ." another lingering glance, this one trailed down your legs, "Don't wanna hurt ya though -" he snorted, "- and that's the problem isn't it. What are you doing to me?" 

He seemed a little angry about it.

"I'm not. . I don't know," you swallowed meekly, "Please don't be angry. ." and his eyes snapped to the side of your face,

"Not angry," he rumbled, shifting in his seat as if the lie made him uncomfortable. After a moment of heavy silence he pulled the sleek ride off of the highway and onto an unmarked gravel road,

"What - what are you doing?" God your voice betrayed your panic like Cain did Abel. No answer. Again. "Dean." the leather of the seat by your thighs was being squeezed ruthlessly by your little fists. Of course Dean couldn't see that under the musty blanket.

Was he about to fuck you again? Of course there was no denying your supreme attraction to this man, but you were so sore down there that the idea of having sex made your tummy knot up like you were back in that kitchen.

"Dean," after being ignored yet again, you forgot all sense of self and threw a punch to the demon's shoulder. Apparently you needed his attention so badly that you were willing to die for it. The brakes were slammed so hard, that you flew into the dashboard - seat belt be damned - and the car skidded about ten feet before resting. 

Without so much as a second thought, you threw yourself out of the car and into the gravel to get away from the beast that was no doubt about to "tag you back". When you heard his door slam and gravel crunch under his boots, you began to panic.

But you did so silently, curling up against the purring ride with your hands over your eyes like some kind of toddler. 

The blanket was still halfway in the passenger seat, so the only thing that was blocked from view was your breasts and one shoulder. The crunching stopped right beside you. 

"Thought it was a good idea to hit me, huh?" he asked it casually, like he was talking about the weather,

"You - I - you were ignoring me," you whispered meekly, and you heard him hum agreeably,

"Well," he seemed to be thinking hard about something, "In the grass or on top of the hood?" you swallowed, whining fearfully,

"Wh-what?" 

"The car or the grass princess." he repeated impatiently,

"What are you talking about?!" you finally uncovered your eyes, deciding that being in the dark was much more scary than looking at him. He was smiling softly. It clearly dared you to ask him to repeat the question for a third time. So you said weakly,

"C-car." and with a single nod he was hauling you up and away from the blanket, to plop you down on the hood a little roughly,

"Good choice." he licked his lips and gave an eye crinkling tight lipped smile,

"What are we doing out here?" you crossed your arms over yourself, "Why did we stop?" with one finger, Dean turned your head to make you look at a cement structure that was half buried in the ground. It looked to be part of a hill or something. . Like a bomb shelter maybe.

"Well, no sense in continuing on if we made it home," he muttered and let go of your face, "As for what we're doing. . well you and I gotta say goodbye." and while the words were spoken harshly, Dean's eyes flashed with a secret emotion. It looked a Hell of a lot like sadness.

Your heart panged, "What? I thought you said -" 

"Only for a while. I'm. ." he appeared to be searching for words, "Fuck what are you doin' to me?" he asked again, but you stayed quiet, reeling over the fact that you were upset about the prospect of being abandoned by Dean. The demon who tortured you. Raped you in more ways than one. "I'm no good for you sweetheart." he finally said.

"But -"

"It isn't safe. Not with me." the look in his eye, so intense - sincere - that it made you crack, and made your (e/c) eyes fill. _What. . Why do I care? Get away from him crazy!!_ "But you can bet on one one thing baby girl." you shivered at the name, "I'm gonna be visiting you and your tight little pussy from time to time. . checkin' up on you. Gotta make sure you stay out of trouble, you know why?" 

"Why Dean?" you were leaning forward, as was he, until your lips were so close that they were brushing.

"Because your mine. These lips," he kissed you quick, "these tits, "he gripped your breasts hard enough to make you gasp, "and this cunt." those hands moved down to roughly cup you possessively and you felt arousal spark along with lingering ache. "Say it." 

"I'm yours." it was a breathy whisper, and the giant leaned back down to claim your lips once again. It was slow, sensual, and full of meaning.

The kiss was so mesmerizing, that you didn't even notice the burn of the metal grabbing at your naked skin when Dean pulled you to the edge of the hood, so good that you didn't register the zipper on his jeans ringing as he took it down. .

Only when you felt his familiar thickness at your entrance, did you realize what he meant by "say goodbye". Only this time you weren't frightened. Dean entered you swiftly with a soft grunt and the pain, while still there, was dull and achy instead of sharp and demanding like before.

"Dean. . Yessss." 

You molded around him rather quickly, and he hooked his arms around your knees and lifted you from the car by your legs.

Holding you to his front with hands braced on your ass, Dean fucked into you, holding you like some sort of over-sized doll. The big man was even pulling you in to meet each thrust, and all you had to do was lay your head on his shoulder for the ride.

Dean was so fucking strong. . it was incredibly sexy.

"God baby," he grunted, hitting your clit with his pubis on every thrust. "M'gonna have to come by sooner rather than later." he stepped forward and dropped you back onto the hood, where you flopped backward like a rag doll, but he kept a hold on your legs and continued his deep rhythmic thrusting. 

Your climax surprised you, but it was like your body was so tired that it was subtle. Like the echos of thunder rather than the one crashing right above your head, and when your pussy spasmed it was weak and gentle. Still Dean had no trouble coming himself, once again pushing that hot seed deep inside of you. . it made you worry for a fleeting moment.

"I might miss you sweetheart. My little fuck toy from Crowley. . at least he did somethin' right." he righted himself back into his jeans and gently lifted you from the hood to set you on your own two feet, chuckling when you winced and wobbled,

"Dean. ." you moaned like a tired child,

"Shh, shh," he leaned down to kiss the top of your head, and then turned you toward the bizarre looking building,

"My brother's in there. His name's Sammy and he's gonna take care of you while I'm gone. He'll protect you, cause well. . he's a sappy little shit. There's no way he's turning away some beaten naked girl on his doorstep." you shivered, wondering if Dean registered that he was the reason you looked beaten.

 Dean's body heat disappeared when he backed off of you, and upon turning around you got an oddly encouraging gesture and a small smile from the demon.

"Go on," he coaxed, leaning back to pull his bottom lip into his mouth and whistle, "Goddamn do you got a pretty little ass on you. Gonna redden that up again real soon." and then with an affirmative pat you startled into motion, and began slowly walking on the painful gravel toward the strange metal door.

It took forever to get there, and when you nervously glanced back to see Dean he was watching you from the windshield in the driver's seat. Already having angled the old car to point down the highway. Your heart panged. _Why does this hurt so much? Shouldn't you want to escape?_

You shook your head, swallowing hard when Dean's gaze turned icy. Then promptly turning around and knocking when his eyes flashed to black. 

Standing there with no clothes and no cover, you hunched slightly over in front of the heavy duty door, trying your best to hide your bruised breasts and squeezing your thighs together for some sense of protection. _Cause why wouldn't Dean's brother be fucked in the head too?_

Vibrations indicating life on the other side of the door made you step back nervously. And when it groaned open to reveal a shotgun barrel aimed right at your chest you took four more steps back nervously,

"Wait! Your brother Dean - he kidnapped and f-fucked me!" you cried, staring at the ground through scared and shamed tears. No point in sugar coating it now though, "I - I've been tortured - he said you would protect me! Please don't kill me!" the gun barrel immediately dropped,

"Holy shit." someone breathed, and without looking up you asked,

"Are you S-Sammy?" a long pause occurred where you could feel yourself being gawked at,

"It's Sam actually." and then you finally raised your eyes, only to outright gasp at the beast of a man you saw. You whirled to find Dean, only to see empty dirt road. The car was gone - he was gone - he had left you with this monster of a human.

All at once you felt empty inside, craving the demon that destroyed you. That made you his,

"Hey," Sam spoke softly, and you jumped at feeling his giant paw on your shoulder, "Let's get you some clothes. . and a shower, how does that sound?" you turned back to find him staring 100 feet down on you with soulful hazel flecked eyes.

_Oh my God, it's a fucking giant._

**Notes for the Chapter:**

> Alright comments and suggestions are always welcome down here! I love to hear from ya ;) 
> 
> Thank you for reading, I hope the last chapter was worth the wait!! :) I'm happy it's over but sad to see it go!! Midnight On A Saturday is up next for those of you following it <3
> 
> Loves! <3
> 
> Come kink with me on Twitter @DirtyMind_Girl ;)


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